USPTO Patents Application 10728088

Access DBM

SEARCH REQUEST FORM

Scientific and Technical Information Center

Requester's Full Name: . D\l Examiner # ; ^^^5^ Date

jj^lL Phone Number 3 0 A ^ Serial Number: L/ ^

BIdg/Room Location: 1^1? Yj Results Foraiat Preferred (circle):

Art Unit;

Mail Box and Bldg/Room Location: I^T> Results Foraiat Preferred (circlej: ^XpER'SiSK E-MAIL
If more than one search is submitted^ please prioritize searches In order of need.

Please provide a detailed statement of the search topic, and describe as specifically as possible the subject matter to be searched.
Include the elected species or structures, keywords, synonyms, acronyms, and registry numbers, and combine with the concept or
utility of the invention. Define any terms that may have a special meaning. Give examples or relevant citations, authors, etc, if
known. Please attach a copy of the cover sheet, pertinent claims, and abstract.

Title of Invention:

Inventors (please provide full names):

Earliest Priority Filing Date: _J

"For Sequence Searches Only* Please include all pertinent informaHon (parent, child, divisional, or issued patent numbers) along with the
appropriate serial number,

SCIENTiriC REFERENCE Bf
Sci ^ iec»7 Inf. Cn»

Pat. & T.IVI. Of'ice

STAFF USE OP

Searcher:

Searcher Phone #: _
Searcher Location:

Date Searcher Picked Up:

Date Coinpleted: ^-2jZ-At^

Searcher Prqi A Review Time: _

Clerical Prep Tinie:

Online Time:

Type of Search

NA Sequence (#)

AA Sequence (#)

Stn]cturc(#) .

Bibliographic

Litigation

Fulltext

Patent Family

Other

Vendors and cost where applicable

STN

Dialog .

Questcl/Orbit_
Dr. Link

Lexis/Nexis

Sequence Systems _

www/Internet

Other (speciiy)

PTO-1590(8.01)

WHAT IS CZAIMED IS:

1. A process for preparing conductive polythiophenes
comprised of structural units of the general formula (1) :

5

(1)

where Ri and R2 independently represent hydrogen or a C1-C4
alkyl group, or together represent an optionally substituted
C1--C4 alkylene group, preferably an optionally alkyl-
10 substituted methylene group, an optionally Ci'-C^ alky- or
phenyl -substituted 1,2-ethylene group, a 1 , 3-propylene group
or a 1, 2-cyclohexylene group;

which are prepared from 2 , 5-dihalothiophene of the general
formula (2) :

15

where Ri and R2 are described as above in the general
formula (1), and X is a halogen atom selected from Cl, Br
and I;

20 in the presence of an acid catalyst •

15

4- t>

2. A process for preparing polythiophenes according to
claim 1, wherein Ri and R2 independently represent methylene,
1,2 -ethylene or 1, 3 -propylene,

5 3 . A process for preparing poly thiophene according to

claim 1 or 2, wherein the acid catalyst is a Lewis acid,
protic acid, organic acid or polymeric acid.

4 . A process for preparing polythiophenes according to
10 claim 3, wherein the Lewis acid catalyst is a boron salt,

zinc salt, tin salt or iron salt; the protic acid catalyst
is phosphoric acid^ sulfuric acid, nitric acid, hypochlorous
acid, HF, HCl, HBr or HI; the organic acid catalyst is
carboxylic acid or sulfonic acid; polymeric acid catalyst is
15 polystyrenesulf onic acid, polyacrylic acid, polymethacrylic
acid, polymaleic acid or polyvinylsulf onic acid; and the
catalyst is used individually or as a mixture of two or more.

5 . A process for preparing polythiophenes according to
20 claim 4, wherein the boron salt is boron trifluoride, boron

tri fluoride dihydrate, boron trifluoride diethyl etherate,
boron tri fluoride-alcohol complex, boron tri fluoride-methyl
sulfide complex, boron tri fluoride-phosphoric acid complex,
boron trichloride, boron trichloride-methyl sulfide complex,
25 boron tribromide, or boron tribromide -methyl sulfide complex,

16

used individually or as a mixture of two or more.

6. A process for preparing polythiophenes according to
any one of claims 1 to 5, wherein the solvent is a C6-C20

5 aliphatic or aromatic hydrocarbon, halogen-containing
hydrocarbon, ketone, ether, C2~C2o alcohol, sulfoxide, amide
and water, or a mixture thereof.

7 . A process for preparing poly thiophene according to
10 claim 6, where the solvent is a Ce-Cao aliphatic or aromatic

hydrocarbon including alkanes, alkylbenzenes and phenol;
halogen-containing hydrocarbon including alkanes and
halobenzenes containing halogen substituent (s) ; ketone
including acetone, propanone, butanone, pentanone, hexanone,

15 heptanone, octanone and acetophenone; ether including
diethyl ether, tetrahydrofuran (THF) , dipropyl ether,
dibutyl ether, methyl butyl ether, diphenyl ether, dioxane,
diglyme, diethylene glycol and ethylene glycol (EG) ;
sulfoxide including dimethyl sulfoxide (DMSO) ; amide

20 including N,N-dimethylformamide (DMF) , N-methylacetamide
(NMAA) , N,N-dime thy lace tamide (DMA) , N-methylpropionamide
(NMPA) and N-methylpyrrolidinone (NMP) , used either
individually or as a mixture of two or more.

25

17

Truong 10/728,088

Page 1

=> file reg
FILE 'REGISTRY'

USE IS SUBJECT TO THE TERMS OF YOUR STN CUSTOMER AGREEMENT.
PLEASE SEE "HELP USAGETERMS" FOR DETAILS.
COPYRIGHT (C) 2005 American Chemical Society (ACS)

=> d his

FILE 'LREGISTRY'
LI STR
L2 STR LI

FILE 'REGISTRY'

L3

2

S

LI

L4

SCR 2043 OR 1976

L5

10

S

LI AND L4

L6

633

S

LI AND L4 FUL

SAV L6 TRU088/A

L7

483

S

L6 AND PMS/CI

L8

227

S

L6 AND KX

L9

77

S

L7 AND L8

LIO

6

s

L2 SSS SAM SUB=L6

Lll

48

s

L2 SSS FUL SUB=L6

SAV Lll TRU088A/A

L12

26

S

Lll AND L7

L13

22

S

Lll NOT L12

L14

457

S

L7 NOT L12

FILE 'HCA'

L15

29

s

L12

L16

30

s

L13

L17

2609

s

L14

L18

15

s

L16 AND L17

L19

4

s

L15 AND ACID?

L20

4

s

LI 6 AND ACID?

L21

44383

s

LEWIS#

L22

10868

s

BRONSTED# OR BROENSTED#

L23

1

s

L15 AND (L21 OR L22)

L24

0

s

L16 AND (L21 OR L22)

L25

6

s

L19 OR L20 OR L23

L26

29

s

(LIS OR L18) NOT L25

L27

26

s

LI 6 NOT L25

L28

4

s

L16 NOT (L26 OR L27)

FILE 'REGISTRY'

Truong 10/728,088 Page 2

=> d 111 que Stat
LI STR

7 0 0 8

Cwvv^C

6 "^v^ 4
S
5

NODE ATTRIBUTES:
DEFAULT MLEVEL IS ATOM
DEFAULT ECLEVEL IS LIMITED

GRAPH ATTRIBUTES:

RING(S) ARE ISOLATED OR EMBEDDED
NUMBER OF NODES IS 7

STEREO ATTRIBUTES: NONE
L2 STR

7 0 0 8

CWVN/^ C

6 C ^ C

V rT ^

10 Gl . S Gl 9

VAR G1=CL/BR/I
NODE ATTRIBUTES:
DEFAULT MLEVEL IS ATOM
DEFAULT ECLEVEL IS LIMITED

GRAPH ATTRIBUTES:

RING(S) ARE ISOLATED OR EMBEDDED

NUMBER OF NODES IS 9

STEREO ATTRIBUTES: NONE

L4 SCR 2043 OR 1976

L6 633 SEA FILE=REGISTRY SSS FUL LI AND L4

Lll 48 SEA FILE=REGISTRY SUB=L6 SSS FUL L2

100.0% PROCESSED 65 ITERATIONS

48 ANSWERS

Truong. 10/728, 088

Page

SEARCH TIME: 00.00.01

=> file hca
FILE 'HCA'

USE IS SUBJECT TO THE TERMS OF YOUR STN CUSTOMER AGREEMENT.
PLEASE SEE "HELP USAGETERMS" FOR DETAILS.
COPYRIGHT (C) 2005 AMERICAN CHEMICAL SOCIETY (ACS)

=> d 125 1-6 cbib abs hitstr it jj

L25 ANSWER 1 OF 6 HCA COPYRIGHT 2005 ACS on STN •
141:226365 Processes for preparing conductive macromolecular

polythiophenes using acid catalysts. Baik, Woon-phil;

Kim, Young-sam; Park, Jae-han; Jung, Sang-gook (Myongji University,

S. Korea)'. U.S. Pat. Appl. Publ. US 2004171790 AA 2-00'4lD'9O2 , 5 pp.

(English). CODEN: USXXCO. APPLICATION: US 2003-^8088 20031205.

PRIORITY: KR 2002-77465 20021206, V ^

RlO 0R2

I

AB The polythiophene I (Rl, R2 = H, (un) substituted Cl-4 alkyl,

(un) substituted 1, 2-ethylene, 1, 3-propylene or 1, 2-cyclohexylene
group) is prepd. by cationic polymn. from 2, 5-dihalothiophene in the
presence of an acid catalyst, such as Lewis
acid, protic acid, oxygen acid, or

polymeric acid. The cond. of the resulting polythiophene

is 255 S/cm under optimal conditions. Thus, 20.0 g

2, 5-dibromo-3, 4-ethylenedioxythiophene was mixed with toluene 400

and boron trifluoride 2 6 mL at room temp, for 4 h and heated to

100° for 24 h to give 12.9 g poly (3, 4-ethylenedioxythiophene)

which having cond. 255 S/cm.

IT 350037-71-7P 748185-34-4P 748185-35-5P

(processes for prepg. conductive macromol. polythiophenes using
acid catalysts)

RN 350037-71-7 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2, 3~dihydro-, homopolymer
(9CI) (CA INDEX NAME)

Truong 10/728,088

Page 4

CM

CRN
CMF

174508-31-7
C6 H4 Br2 02 S

Br

748185-34-4 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 2, 3-dihydro-5, 7-diiodo-, homopolymer (9CI)
(CA INDEX NAME)

CM 1

CRN 640737-72-0
CMF C6 H4 12 02 S

CN Thiophene, 2, 5-dibromo-3, 4-dimethoxy-, homopolymer (9CI) (CA INDEX
NAME)

CM 1

CRN 345666-04-8 ' '

CMF C6 H6 Br2 02 S

RN

748185-35-5 HCA

Truong 10/728, 088

Page 5

IT Polymerization catalysts

(cationic; processes for prepg. conductive macromol.
polythiophenes using acid catalysts)
IT Acids, uses

(org*; processes for prepg. conductive macromol. polythiophenes
using acid catalysts)
IT Acids, uses

Carboxylic acidS/ uses

Lewis acids
Sulfonic acids, uses

(processes for prepg. conductive macromol. polythiophenes using
acid catalysts)

IT 109-63-7, Boron trifluoride diethyl etherate 353-43-5 1428-24-6,
Boron trif luoride-triphenyl phosphate complex (1:1) 5523-19-3,
Boron trichloride-dimethyl sulfide (1:1) 7439-89-6D, Iron, salts
7440-31-5D, Tin, salts 7440-42-8D, Boron, salts 7440-66-6D,
Zinc, salts 7637-07-2, Boron trifluoride, -uses 7646-85-7, Zinc
chloride, uses 7647-01-0, Hydrochloric acid, uses
7664-38-2, Phosphoric acid, uses 7664-39-3, Hydrofluoric
acid, uses 7664-93-9, Sulfuric acid, uses
7697-37-2, Nitric acid, uses 7790-92-3, Hypochlorous
acid 9003-01-4, Polyacrylic acid 10034-85-2,
Hydroiodic acid 10035-10-6, Hydrobromic acid,

uses 10294-33-4, Boron tribromide 10294-34-5, Boron trichloride
13319-75-0, Boron trifluoride dihydrate 25087-26-7,
Polymethacrylic acid 26099-09-2, Polymaleic acid
26101-52-0, Polyvinylsulfonic acid 29957-59-3
50851-57-5, Polystyrenesulf onic acid

(processes for prepg. conductive macromol. polythiophenes using

acid catalysts)
IT 12032 6-42-3P, Poly (3, 5-dimethoxy-2, 5-thiophenediyl)
350G37-71-7P 748185-34-4P 748185-35-5P

(processes for prepg. conductive macromol. polythiophenes using

acid catalysts)

L25 ANSWER 2 OF 6 HCA COPYRIGHT 2005 ACS on STN

139:93393 Characterization of Organic p/n Junction Photodiodes Based on
Poly (alkylthiophene) /Perylene Diimide Bilayers. Tan, Li; Curtis, M.
David; Francis, A. H. (Macromolecular Science & Engineering Center
and Department of Chemistry, The University of Michigan, Ann Arbor,
MI, 48109-1055, USA). Chemistry of Materials, 15(11), 2272-2279
(English) 2003. CODEN: CMATEX . ISSN: 0897-4756. Publisher:
American Chemical Society.

AB Photoconduction of bilayer org. p/n junction photocells can be
finely tuned through the alteration of either the side chain
orientation (regiorandom vs. regioregular ) or main chain structure
in poly (3-alkylthiophene) s (P3ATs) , where the incorporation of an
electron-donating group (EDOT) appears to be an excellent method for

Truong 10/728, 088

Page 6

enhancing the photoconduction. also, doping of P3ATs proved to be an
equally viable. route for tuning the device characteristics. These
polymers were used to fabricate bilayer org. photocells with the
polymer as the p-type layer and 1, 2-diaminobenzeneperylene-3, 4, 9, 10-
tetracarboxylic acid diimide (PV) as the n-type layer.
Action spectra at steady-state illumination demonstrated that all
the interfaces (org. -org. p/n junction and org. -electrode) are
actively involved in the photogeneration of carriers. Crit. device
properties, for example, open-circuit voltage (Voc) and
short-circuit current (Isc), are not only dependent on the selection
of electrodes and org. materials but also greatly affected by the
illumination wavelength and intensity.

IT 554459-31-3P, 2, 5-Dibromo-3-butylthiophene-2 , 5-dibromo-3, 4-
ethylenedioxythiophene copolymer
(prepn. and properties of)

RN 554459-31-3 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2, 3-dihydro-, polymer with
2, 5-dibromo-3-butylthiophene (9CI) (CA INDEX NAME)

CM 1

CRN 174508-31-7
CMF C6 H4 Br2 02 S

Br

CM 2

CRN 116971-10-9
CMF C8 HIO Br2 S

Bu-n

IT 174508-31-7P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene
(prepn. of)

t '

Truong 10/728,088 Page 7

RN 174508-31-7 HCA

CN Thieno[3,4-b]-l,4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

Br

IT Electric current carriers

(generation; properties of org. pn photodiodes based on

polyalkylthiophenes and diaminobenzeneperylenetetracarboxylic

acid diimide)
IT Glass substrates

(in fabrication of org. pn photodiodes based on

polyalkylthiophenes and diaminobenzeneperylenetetracarboxylic

acid diimide)
IT Cyclic voltaminetry

(of polyalkylthiophene derivs.)
IT Band gap

(optical; of polyalkylthiophene derivs.)
IT Conducting polymers

(polythiophenes; properties of org. pn photodiodes based on

polyalkylthiophenes and diaminobenzeneperylenetetracarboxylic

acid diimide)
IT Absorption spectra
Dopants

Electric current-potential relationship
Electrodes

Open circuit potential

Optical absorption

Photoconductivity

Photocurrent

Photodiodes

Short circuits

Solid-solid interface

(properties of org. pn photodiodes based on polyalkylthiophenes
and diaminobenzeneperylenetetracarboxylic acid diimide)
IT Coating process

(spin; in fabrication of org. pn photodiodes based on
polyalkylthiophenes and diaminobenzeneperylenetetracarboxylic
acid diimide)

IT 104-15-4, Toluenesulfonic acid, uses 7647-01-0, Hydrogen
chloride, uses 7664-93-9, Sulfuric acid, uses

f »

Truong 10/728,088 Page 8

14635-75-7, Nitrosonium tetraf luoroborate

(P30T dopant; properties of org. pn photodiodes based on
polyalkylthiophenes and diaminobenzeneperylenetetracarboxylic
acid diimide)
98837-51-5, Poly (3-butylthiophene)

(UV spectra of)
7440-22-4, Silver, uses

(contact; properties of org, pn photodiodes based on
polyalkylthiophenes and diaminobenzeneperylenetetracarboxylic
acid diimide)
116971-10-9, 2, 5-Dibromo-3-butylthiophene

(in prepn. of butylthiophene-ethylenedioxythiophene copolymer)
126213-50-1, 3, 4-Ethylenedioxythiophene

(in prepn. of dibromoethylenedioxythiophene)
554459-31-3P, 2, 5-Dibromo-3-butylthiophene-2, 5-dibromo-3, 4-
ethylenedioxythiophene copolymer

(prepn. and properties of)
174508-31-7P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene

(prepn. of)
50926-11-9, ITO 55034-79-2

(properties of org. pn photodiodes based on polyalkylthiophenes
and diaminobenzeneperylenetetracarboxylic acid diimide)
104934-51-2, Poly (3-octylthiophene)

(pure and doped; properties of org, pn photodiodes based on
polyalkylthiophenes and diaminobenzeneperylenetetracarboxylic
acid diimide)
7664-41-7/ Ammonia, processes

(redn. of doped P30T with; properties of org. pn photodiodes
based on polyalkylthiophenes and diaminobenzeneperylenetetracarbo
xylic acid diimide)

L25 ANSWER 3 OF 6 HCA COPYRIGHT 2005 ACS on STN

137:232315 Optical and redox properties of a series of

3, 4-ethylenedioxythiophene oligomers. Apperloo, Joke J.;
Groenendaal, L. "Bert"; Verheyen, Hilde; Jayakannan, Manickam;
Janssen, Rene A. J.; Dkhissi, Ahmed; Beljonne, David; Lazzaroni,
Roberto; Bredas, Jean-Luc (Laboratory for Macromolecular and Organic
Chemistry, Eindhoven University of Technology, Eindhoven, 5600 MB,
Neth.). Chemistry--A European Journal, 8(10), 2384-2396 (English)
2002. CODEN: CEUJED. ISSN: 0947-6539. OTHER SOURCES: CASREACT
137:232315. Publisher: Wiley-VCH Verlag GmbH.

AB The optical and redox properties of a series of 3,4-

ethylenedioxythiophene oligomers (EDOTn, n = 1-4) and their

(3, p'-unsubstituted analogs (Tn, n = 1-4) are described.

Both series are end capped with Ph groups to prevent irreversible

a-coupling reactions during oxidative doping. Absorption and

fluorescence spectra of both series reveal a significantly higher

degree of intrachain conformational order in the EDOTn oligomers.

Truong 10/728,088 Page 9

Oxidn. potentials (EPAl and EPA2) detd. by cyclic voltammetry reveal
that those of EDOTn are significantly lower than the corresponding
Tn oligomers as a consequence of the electron-donating
3, 4-ethylenedioxy substitution. Linear fits of EPAl and EPA2 vs.
the reciprocal no. of double bonds reveal significantly steeper
slopes for the EDOTn than for the Tn oligomers. This could ' indicate
a more effective conjugation for the EDOTn series, confirmed by the
fact that coalescence of EPAl and EPA2 is reached already at
relatively short chain lengths («5 EDOT units) in contrast
to the Tn series (> 10 thiophene units) . The stepwise chem. oxidn.
of the EDOTn and Tn oligomers in soln. was carried out to obtain
radical cations and dications. The energies of the optical
transitions of the radical cations and dications as detd. by
UV/Vis/NIR spectroscopy were similar for the two series. These
spectroscopic observations are consistent with quantum-chem. calcns.
performed on the singly charged mols. Cooling solns. contg.
T2*+, T3*+, ED0T2*+, and ED0T3*+ revealed the

reversible formation of dimers, albeit with a some-what different
tendency, expressed in the values for the dimerization enthalpy.
IT 174508-31-7P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene

(coupling; prepn. and optical and redox properties of a series of
3, 4-ethylenedioxythiophene oligomers)
RN 174508--31-7 HCA

CN Thieno[3,4-b]-l,4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

Br

Br

IT Radical ions

(cations, formation, electronic and ESR spectra, and
dimerization; prepn. and optical and redox properties of a series
of 3, 4-ethylenedioxythiophene oligomers)

IT Exciton

(coupling in radical cation dimers; prepn. and optical and redox
properties of a series of 3, 4-ethylenedioxythiophene oligomers)
IT Cations

(divalent; prepn. and optical and redox properties of a series of
3, 4-ethylenedioxythiophene oligomers)
IT Substituent effects

(ethylenedioxy; prepn. and optical and redox properties of a
series of 3, 4-ethylenedioxythiophene oligomers)

Truong 10/728, 088

Page 10

CI (molecular orbital method)

Oscillator strength

(in electronic excitation of radical cations; prepn. and optical
and redox properties of a series of 3, 4-ethylenedioxythiophene
oligomers)

Conformation

(intrachain conformational order; prepn. and optical and redox

properties of a series of 3, 4-ethylenedioxythiophene oligomers)
Dimerization
Dimerization enthalpy
ESR (electron spin resonance)
Electronic excitation
Hyper fine coupling

(of radical cations; prepn. and optical and redox properties of a

series of 3, 4-ethylenedioxythiophene oligomers)
Chemical chains
Fluorescence
Homologous series
Oxidation potential
UV and visible spectra
Vibronic excitation

(prepn. and optical and redox properties of a series of

3, 4-ethylenedioxythiophene oligomers)
Oligomers

(prepn. and optical and redox properties of a series of

3, 4-ethylenedioxythiophene oligomers)
Conjugation (bond)

(tt-; prepn. and optical and redox properties of a series of

3, 4-ethylenedioxythiophene oligomers)
29488-24-2, 2-Bromo-5-phenylthiophene

(boronation; prepn. and optical and redox properties of a series

of 3, 4-ethylenedioxythiophene oligomers)
591-50-4, lodobenzene 625-88-7, 2, 5-Diiodothiophene 3339-80-8,
5, 5'-Diiodo-2, 2 '-bithiophene 24 388-2 3-5 104 4 99-99-2,
5,5' '-Diiodo-2,2' :5',2' '.-terthiophene 264282-36-2

(coupling; prepn. and optical and redox properties of a series of

3, 4-ethylenedioxythiophene oligomers)
174508-31-7P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene
4594 09-7 0-2P 4 594 09-71-3P 459409-73-5P 459409-74-6P

(coupling; prepn. and optical and redox properties of a series of

3, 4-ethylenedioxythiophene oligomers)
76-09-5, Pinacol

(cyclocondensation with boronic acid; prepn. and

optical and redox properties of a series of 3,4-

ethylenedioxythiophene oligomers)
205436-42-6 4594 09-82-6

(dimerization; prepn. and optical and redox properties of a

series of 3, 4-ethylenedioxythiophene oligomers)

Truong 10/728, 088

Page 11

IT 1665-32-3P, 5, 5' ' -Diphenyl-2, 2 ' :5' ,2' ' -terthiophene 83495-30-lP,
5, 5'-Diphenyl-2,2'-bithiophene 459409-75-7P 4594 09-76-8P
459409-77-9P

(electro- and chem. oxidn.; prepn. and optical and redox
properties of a series of 3, 4-ethylenedioxythiophene oligomers)

IT 238397-97-2P, 5,5' ' ' -Diphenyl-2 , 2 ' :5',2'':5'\2»' ' -quaterthiophene
(electro- and chem. oxidn*; prepn. and optical and redox
properties of a series of 3, 4-ethylenedioxythiophene oligomers)

IT 1445-78-9P, 2, 5-Diphenylthiophene 459409-78-OP

(electrooxidn. ; prepn. and optical and redox properties of a
series of 3, 4-ethylenedioxythiophene oligomers)

IT 185258-96-2 459409-83-7

(oxidn. and dimerization; prepn. and optical and redox properties
of a series of 3, 4-ethylenedioxythiophene oligomers)

IT 459409-85-9

(oxidn.; prepn. and optical and redox properties of a series of
3, 4-ethylenedioxythiophene oligomers)
IT 4594 09-79-lP 4594 09-80-4P

(prepn. and optical and redox properties of a series of
3, 4-ethylenedioxythiophene oligomers)
IT 459409-81-5 459409-84-8 4 594 09-8 6-0 4 594 09-87-1 4 594 09-88-2
(prepn. and optical and redox properties of a series of
3, 4-ethylenedioxythiophene oligomers)
IT 98-80-6, Phenylboronic acid

(prepn. and optical and redox properties of a series of
3, 4-ethylenedioxythiophene oligomers)
IT 126213-50-1, 3, 4-Ethylenedioxythiophene

(reactions; prepn. and optical and redox properties of a series
of 3, 4-ethylenedioxythiophene oligomers)
IT 459409-72-4P

(reactions; prepn. and optical and redox properties of a series
of 3, 4-ethylenedioxythiophene. oligomers)
IT 195602-17-6

(stannylation; prepn. and optical and redox properties of a
series of 3, 4-ethylenedioxythiophene oligomers)

L25 ANSWER 4 OF 6 HCA COPYRIGHT 2005 ACS on STN

136:279781 Electrochemical, conductive, and magnetic properties of

2, 7-carbazole-based conjugated polymers. Zotti, Gianni; Schiavon,
Gilberto; Zecchin, Sandro; Morin, Jean^Francois; Leclerc, Mario
(Istituto di Polarografia ed Elettrochimica Preparativa, Consiglio
Nazionale delle Ricerche, Padua, 35020, Italy) . Macromolecules,
35(6), 2122-2128 (English) 2002. CODEN: MAMOBX. ISSN: 0024-9297.
Publisher: American Chemical Society.

AB Novel poly (2, 7-carbazole) s (i.e., poly (N-octyl-2, 7-carbazole-diyl)
and poly (N- (4-hexyl-benzoyl) -2, 7-carbazole-diyl) ) and their
alternating thiophene, bi-thiophene, and 3, 4-ethylenedioxy-2, 5-
thienylene copolymers have been investigated by cyclic voltammetry.

Truong 10/728,088

Page 12

UV-vis spectroelectrochem. , electrochem. quartz crystal
microbalance, in-situ ESR, and in-situ cond. techniques. All
polymer films undergo reversible oxidn. and partially reversible
redn. processes. In poly {N~octyl-2, 7-carbazole--diyl) , two
isoelectronic oxidn. .processes produce radical cations and dication
with charge localization at the carbazole subunits. The presence of
a strong electron-withdrawing substituent onto the nitrogen atom in
the homopolymer leads to an increase by 3 orders of magnitude of the
cond. (i.e., 1 + 10-2 S/cm) . Similarly, in alternating
copolymers, the oxidative charge is more delocalized over the
polyconjugated backbone with in-situ conductivities in the range of
4 + 10-2-4 + 10-3 S/cm.
406726-97-4P

(2, 7-carbazole-based conjugated polymers)
406726-97-4 HCA

9H-Carbazole, 9-octyl-2, 7-bis (4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-
2-yl) polymer with 5, 7-dibromo-2, 3-dihydrothieno [3, 4-b] -1, 4-dioxin
(9CI) (CA INDEX NAME)

CM 1

CRN 406726-92-9
CMF C32 H47 B2 N 04

Me- (CH2)7

Me

CM 2

CRN 174508-31-7
CMF C6 H4 Br2 02 S

Br

Br

Truong 10/728, 088

Page 13

IT Cyclic voltammetry

ESR (electron spin resonance)
Optical absorption
Oxidation

Oxidation potential
Polymerization catalysts
Redox potential

(2, 7-carbazole-based conjugated polymers)
IT Polymers, preparation

(conjugated, carbazole group-contg. ; 2, 7-carbazole-based
conjugated polymers)
IT Band gap

Electric conductivity

(electrochem. and optical; 2, 7-carbazole-based conjugated
polymers)
IT Conducting polymers

(polythiophenes, carbazole group-contg.; 2, 7-carbazole-based
conjugated polymers)
IT 75-05-8, Acetonitrile, uses

(2, 7-carbazole-based conjugated polymers)
IT 406726-95-2P 406726-96-3P 406726-97-4P 406726-98-5P

40672 6-99-6P 4 06727-00-2P 406727-01-3P 406727-02-4P
(2, 7-carbazole-based conjugated polymers)
IT 111-83-1, 1-Bromooctane 358-23-6, Trif luoromethanesulf onic
anhydride 5344-78-5, 4-Bromo-3-nitroanisole 5720-07-0,
4-Methoxyphenylboronic acid 25015-63-8, Pinacolborane .
115297-58-0

(2, 7-carbazole-based conjugated polymers)
IT 13606-06-9P, 4, 4 ' -Dimethoxy-2-nitro-l, 1 ' -biphenyl 61822-18-2P,

2, 7-Dimethoxycarbazole 406726-86-lP 406726-87-2P 406726-88-3P
406726-89-4P

(2, 7-carbazole-based conjugated polymers)
IT 50606-95-6, 4-Hexylbenzoyl chloride 102871-58-9,
2, 7-Dichlorocarbazole

(monomer synthesis; 2, 7-carbazole-based conjugated polymers).
IT 406726-90-7P 406726-91-8P 406726-92-9P 406726-93-OP

(monomer; 2 , 7-carbazole-based conjugated polymers)
IT 603-35-0, Triphenylphosphine, uses 7447-41-8, Lithium chloride,
uses 13965-03-2, Bis (triphenylphosphine) palladium dichloride
14221-01-3, Tetrakis (triphenylphosphine) palladium

(polymn. catalyst; 2, 7-carbazole-based conjugated polymers)

L25 ANSWER 5 OF 6 HCA COPYRIGHT 2005 ACS on STN

131:5811 Temperature-dependent electrical conductivity of p-doped
poly (3, 4-ethylenedioxythiophene) and poly {3-alk:ylthiophene) s .
Yamamoto, Takakazu; Abla, Mahmut; Shimizu, Takahisa; Komarudin,
Dahrma; Lee, Bang-Lin; Kurokawa, Eriko (Research Laboratory

Truong 10/728,088

Page 14

Resources Utilization, Tokyo Institute Technology, Yokohama, 226,

Japan), Polymer Bulletin (Berlin), 42(3), 321-327 (English) 1999.

CODEN: POBUDR. ISSN: 0170-0839. Publisher: Springer-Verlag .
AB Temp . -dependent elec. cond. of the substituted polythiophenes

poly (3, 4-ethylenedioxythiophene) (PEDOTh) and head-to-tail type

poly (3-alkylthiophene) (HT-P3RTh) was measured. The elec. cond.

(a) of p-doped PEDOTh and HT-P3RTh obeys equations of a type.

In o = In aO - (T0/T)0.25, with the TO value of

«105-107 K.
IT 225518-50-3P

(iodine- and iron tetrachloride-doped; temp . -dependent elec.
cond. of p-doped substituted polythiophenes)
RN 225518-50-3 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dichloro-2, 3-dihydro-, homopolymer
(9CI) (CA INDEX NAME)

CM 1

CRN 225518-49-0
CMF C6 H4 C12 02 S

CI

IT 225518-49-OP

(monomer; temp. -dependent elec. cond. of p-doped substituted

polythiophenes )
RN 225518-49-0 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dichloro-2, 3-dihydro- (9CI) (CA INDEX
NAME)

CI

IT Polymers, properties

(polythiophenes; temp. -dependent elec. cond, of p-doped

Truong 10/728,088

Page 15

substituted polythiophenes)
IT Conducting polymers

Electric conductivity

(temp. -dependent elec. cond, of p-doped substituted
polythiophenes )

IT 7553-56-2; Iodine, uses 14946-92-0, Iron tetrachloride

(dopant; temp. -dependent elec. cond. of p-doped substituted
polythiophenes)

IT 110134-47-9, Poly (3-hexyl-2, 5-thiophenediyl)- 135899-67-1,
3-Thiophenepropanesulfonic acid homopolymer 216318-88-6,
Poly ( 3-methyl-2 , 5-thiophenediyl )

(doped; temp . -dependent elec. cond. of p-doped substituted

polythiophenes)
IT 126213-50-lP

(in prepn. of dichloro thiophene monomer)
IT 163359-60-2P 225518-50-3P

(iodine- and iron tetrachloride-doped; temp . -dependent elec.

cond. of p-doped substituted polythiophenes)
IT 225518-49-OP

(monomer; temp. -dependent elec. cond. of p-doped substituted

polythiophenes)

L25 ANSWER 6 OF 6 HCA COPYRIGHT 2005 ACS on STN

82:170765 Methylenedioxyhetarenes . 2. Reactions of diethyl

3, 4-methylenedioxy-2, 5-thiophenedicarboxylate . Dallacker, Franz;

Mues, Volker (Inst. Org, Chem., Tech. Hochsch. Aachen, Aachen, Fed.

Rep. Ger.). Chemische Berichte, 108(2), 576-81 (German) 1975.

CODEN: CHBEAM. ISSN: 0009-2940. OTHER SOURCES: CASREACT 82:170765.
GI For diagram(s), see printed CA Issue.

AB The sym. thiophene deriv. I (R = Rl = C02Et) (II) was treated with

excess ale. KOH, N2H4.H20, and Br at pH 7.0 to give .apprx.100% I (R
= Rl = C02H) (III), 79% I (R = Rl = C0NHNH2 ) (IV), and extremely
light- and air-sensitive I (R = Rl = Br) (V), resp. Ill was
esterified to give I (R = Rl = C02Me) or chlorinated and aminated,
e.g. with NH3, to give I (R = Rl = C0NH2) (VI) . IV was condensed
with piperonal to yield the piperonylidene deriv. I (R = Rl =
CONHN:CHC6H302CH2-3, 4) and V converted into I (R = Rl = iodo) . .
Boiling VI and P0C13 gave 54% I (R = Rl - CN) , which with H2S in
pyridine-Et3N gave 100% I (R = Rl = CSNH2) .

IT 55370-18-8P 55370-19-9P
(prepn. of)

RN 55370-18-8 HCA

CN Thieno[3, 4-d]-l, 3-dioxole, 4, 6-dibromo- (9CI) (CA INDEX NAME)

Truong 10/728,088

Page 16

Br

Br

0

RN 55370-19-9 HCA

CN Thieno [3, 4-d] -1, 3-dioxole, 4,6-diiodo- (9CI) (CA INDEX NAME)

0

IT 55370-05-3

(bromination and hydrazinolysis and hydrolysis of)

IT - 55370-20-2P

(prepn. and decarboxylation and esterif ication and reaction with

thionyl chloride)
IT 55370-12-2P 55370-24-6P

(prepn. and dehydration of)
IT 55370-26-8P 55370-28-OP

(prepn. and hydrolysis of)
IT 55370-11-lP

(prepn. and reaction with amines)
IT 55370-06-4P

(prepn. and reaction with bromine and methanol and thionyl

chloride)
IT 55370-08-6P

(prepn. and reaction with piperonal)
IT 55370-3G-4P

(prepn. and reaction with sodium sulfide)
IT 55370-07-5P 55370-09-7P 55370-10-OP 55370-13-3P 55370-14-4P
55370-15-5P 55370-16-6P 55370-17-7P 55370-18-8P
55370-19-9P 55370-21-3P 55370-22-4P 55370-23-5P
55370-25-7P 55370-27-9P 55370-29-lP 55370-31-5P

(prepn. of)
IT 120-57-0

(reaction of, with (methylenedioxy) thiophenecarbohydrazide)
IT 100-61-8

(reaction of, with (methylenedioxy) thiophenedicarboxylic

Truong 10/728, 088

Page 17

acid)
IT 30525-89-4

(reaction of, with dibromobutanediol)
IT 14396-65-7

(reaction of, with formaldehyde)
IT 110-89-4, reactions

(with (methylenedioxy) thiophenedicarboxylic acid)

=> d 127 1-26 cbib abs hitstr it

L27 ANSWER 1 OF 26 HCA COPYRIGHT 2005 ACS on STN

141:380500 Spray Coatable Electrochromic Dioxythiophene Polymers with
High Coloration Efficiencies, Reeves, Benjamin D.; Grenier,
Christophe R. G.; Argun, Avni A.; Cirpan, Ali; McCarley, Tracy D.;
Reynolds, . John R. (Department of Chemistry, Center for
Macromolecular Science and Engineering, University of Florida,
Gainesville, FL, 32611-7200, USA). Macromolecules, 37(20),
7559-7569 (English) 2004. CODEN: MAMOBX. ISSN: 0024-9297.
Publisher: American Chemical Society.

AB Four new disubstituted propylenedioxythiophene polymers have been

synthesized by Grignard metathesis on the 1-5 g scale. All polymers
were found to be sol. in chloroform, methylene chloride, toluene,
and THF and were fully structurally characterized having GPC detd.
no.-av. mol. wts. ranging from 33000 to 47000 g mol-1. Dil. polymer
solns. in toluene exhibited strong red fluorescence with moderate
quantum efficiencies from 0.38 to 0.50. Homogeneous thin films were
formed by electropolymn. and spray casting polymer solns. onto ITO
coated glass slides at thicknesses of ca. 150 nm. The films were
electroactive, switching from a dark blue-purple to a transmissive
sky blue upon p-doping, often with subsecond switching times, and
high electrochromic contrast luminance changes (% AY) of
40-70%. These studies revealed that the branched derivs.,
[poly (3, 3-bis (2-ethylhexyl) -3, 4-dihydro-2H-thieno [3, 4-
. b] [1, 4]dioxepine) ] and [poly (6, 8-dibromo-3, 3-bis (2-

ethylhexyloxymethyl) -3, 4-dihydrO"-2H-thieno [3, 4-b] [1, 4] dioxepine) ] ,
gave an electrochem. response and assocd. color change over a much
smaller voltage range in comparison to the linear chain substituted
derivs . , [poly (3, 3-dihexyl-3, 4-dihydro-2H-thieno [3, 4-
b] [1, 4]dioxepine) ] and [poly (3, 3-bis (octadecyloxymethyl) -3, 4-dihydro-
2H-thieno [3, 4-b] [1, 4 ] dioxepine) ] . Composite coloration efficiency
values were found up to 1365 cm2/C; this was considerably larger
than values obtained from previously studied alkylenedioxythiophene
based polymers (.apprx.375 cm2/C) .

IT 700817-04-5P 700817-06-7P 700817-08-9P
700817-10-3P

(monomer; prepn. and electrooptical properties of spray coatable
electrochromic dioxythiophene polymers)

Truong 10/728,088

Page

RN 700817-04-5 HCA

CN 2H-Thieno [3, 4-b] [ 1, 4 ] dioxepin, 6, 8-dibronio-3, 3-dihexyl-3, 4-dihydro-
(9CI) (CA INDEX NAME)

Me- (CH2)5
Me- (CH2)5

RN 700817-06-7 HCA

CN 2H-Thieno [3, 4-b] [1, 4] dioxepin, 6, 8-dibromo-3, 3-bis (2-ethylhexyl) -3, 4
dihydro- (9CI) (CA INDEX NAME)

RN 700817-08-9 HCA

CN 2H-Thieno [3, 4-b] [1, 4]dioxepin, 6, 8-dibronio-3, 3-bis [ [ (2-

ethylhexyl) oxy] methyl] -3, 4-dihydro- (9CI) (CA INDEX NAME]

RN 700817-10-3 HCA

CN 2H-Thieno [3, 4-b] [1, 4] dioxepin, 6, 8-dibromo-3, 4-dihydro-3, 3-
bis[ (octadecyloxy) methyl]- (9CI) (CA INDEX NAME)

Truong 10/728, 088

Page 19

Br

Me- (CH2) 17-0-CH2
Me- (CH2) 17-0- CH2

IT Polymerization

(Grignard; prepn. and electrooptical properties of spray coatable

electrochromic dioxythiophene polymers)
IT Polymerization

(electrochem. ; prepn. and electrooptical properties of spray

coatable electrochromic dioxythiophene polymers)
IT Band gap

(optical; prepn. and electrooptical properties of spray coatable
electrochromic dioxythiophene polymers)
IT Conducting polymers

(polythiophenes; prepn. and electrooptical properties of spray
coatable electrochromic dioxythiophene polymers)
IT Elect rochromism

Luminescence, elect roluininescence
Redox potential

(prepn. and electrooptical properties of spray coatable
electrochromic dioxythiophene polymers)
IT Electrooptical effect

(switching; prepn. and electrooptical properties of spray
coatable electrochromic dioxythiophene polymers)
IT 104-76-7, 2-Ethyl-l-hexanol 105-53-3, Diethyl malonate 111-25-1,
Hexyl bromide 112-92-5, 1-Octadecanol 3296-90-0,
2, 2-Di (bromomethyl) -1, 3-diol 18908-66-2, 2-Ethylhexyl bromide
51792-34-8, 3, 4-Dimethoxythiophene

(monomer synthesis; prepn. and electrooptical properties of spray
coatable electrochromic dioxythiophene polymers)
IT 54 662-33-8P 634591-75-6P 634591-77-8P 700816-90-6P
701209-98-5P

(monomer synthesis; prepn. and electrooptical properties of spray

coatable electrochromic dioxythiophene polymers)
IT 700816-98-4P 700817-00-lP 700817-04-5P
700817-06-7P 700817-08-9P 700817-10-3P

(monomer; prepn. and electrooptical properties of spray coatable

electrochromic dioxythiophene polymers )
IT 700817- 12- 5P 7 00817-14-7P 7 008 17-1 6-9P 7 008 17- 18- IP
7 83322-8 0-5P 7 8 3322-81-6P 7 83322-82-7P 7 8 3322- 83- 8P

(prepn. and electrooptical properties of spray coatable

electrochromic dioxythiophene polymers)

Truong 10/728, 088

Page 20

L27 ANSWER 2 OF 26 HCA COPYRIGHT 2005 ACS on STN
141:314660 Synthesis and polymerization of perf luoroalkylated

3, 4-propylenedioxythiophene . Dong, Jian-Hai; Meng, Wei-Dong; Qing,
Feng-Ling (Coll, Chem, Chem, Eng., Donghua Univ., Shanghai, 200051,
Peop. Rep. China). ARKIVOC (Gainesville, FL, United States) (9),
9-14 (English) 2004. CODEN: AGFUAR, URL: http : //www . ar kat-
usa.org/ark/journal/2004/Yuan/CY-1037L/CY-1037L.pdf Publisher:
Arkat USA Inc. .

AB A novel monomer, perf luoroalkylated 3, 4-propylenedioxythiophene, was
prepd, by trans-etherif ication reaction between 3,4-
dimethoxythiophene and perf luoroalkylated cycloalkylpropane-1, 3-
diol. Bromination of monomer followed by a Grignard metathesis
coupling reaction provided perf luoroalkylated poly(3,4-
propylenedioxythiophene) . This polymer was quite insol . in any
known solvent.
IT 768400-95-9P

(multi-step prepn. of perf luoroalkylated propylenedioxythiophene
monomer and its bromination followed by Grignard metathesis
coupling polymn.)
RN 768400-95-9 HCA

CN Spiro[cyclopentane-l,3' (4 'H) - [2H] thieno [3, 4-b] [ 1 , 4 jdioxepin] ,
6' , 8 ' -dibromo-3-methyl-4- (2, 2, 3, 3, 4, 4, 5, 5, 6, 6, 7, 7, 7-
tridecafluoroheptyl) - (9CI) (CA INDEX NAME)

Br

IT Polymerization

(Grignard, metathetic; multi-step prepn. of perf luoroalkylated
propylenedioxythiophene monomer and its bromination followed by
Grignard metathesis coupling polymn.)

IT Polymerization

(metathetic, Grignard; multi-step prepn. of perf luoroalkylated
propylenedioxythiophene monomer and its bromination followed by
Grignard metathesis coupling polymn.)

IT 3195-24-2P, Diethyl 2, 2-diallylmalonate

(cyclization of; multi-step prepn. of perf luoroalkylated
propylenedioxythiophene monomer and its bromination followed by
Grignard metathesis coupling polymn.)

IT 768400-93-7P *

Truong 10/728, 088

Page 21

(cycloaddn. of; multi-step prepn. of perf luoroalkylated
propylenedioxythiophene monomer and its bromination followed by
Grignard metathesis coupling polymn.)

105-53-3, Diethyl malonate 106-95-6, Allyl bromide, reactions

355-43-1, Perf luorohexyl iodide 51792-34-8, 3, 4-Dimethoxythiophene
(multi-step prepn* of perf luoroalkylated propylenedioxythiophene
monomer and its bromination followed by Grignard metathesis
coupling polymn.)

768400-94-8P 768400-95-9P

(multi-step prepn. of perf luoroalkylated propylenedioxythiophene
monomer and its bromination followed by Grignard metathesis
coupling polymn.)

768400-96-OP

(multi-step prepn. of perf luoroalkylated propylenedioxythiophene
monomer and its bromination followed by Grignard metathesis
coupling polymn.)
169893-13-4P

(redn. of; multi-step prepn. of perf luoroalkylated
propylenedioxythiophene monomer and its bromination followed by
Grignard metathesis coupling polymn.)

ANSWER 3 OF 2 6 HCA COPYRIGHT 2005 ACS on STN

89456 Copolymers of 3, 4-Ethylenedioxythiophene and of Pyridine

Alternated with Fluorene or Phenylene Units: Synthesis, Optical
Properties, and Devices. Aubert, Pierre-Henri; Knipper, Martin;
Groenendaal, Lambertus; Lutsen, Laurence; Manca, Jean; Vanderzande,
Dirk (IMOMEC Division, IMEC, Diepenbeek, B-3590, Belg.).
Macromolecules, 37(11), 4087-4098 (English) 2004. CODEN: MAMOBX.
ISSN: 0024-9297. Publisher: American Chemical Society.
We report the synthesis of four conjugated copolymers based on
alkylated fluorene or phenylene units which band gap is tuned by the
regular insertion of an electron-donating or electron-withdrawing
unit, (3, 4-ethylenedioxy) thiophene and pyridine, resp. The (AB)n
regular sequence is achieved by Suzuki polycondensation reactions.
The characterization of the copolymers by size exclusion chromatog.
reveals chains lengths of about 20-30 repeat units (40-60 rings),
leading to a good processability for potential optical applications.
The 1:1 ratio between the two units improves the soly. of the
material in common org. solvents, allowing for physicochem.
characterizations. Raman and FT-IR expts. indicate that the
electronic structure of the backbone is rather benzenic in the
neutral (undoped) state, as opposed to a quinoic oxidized structure.
All copolymers exhibit interesting electrochromic properties as
attested by cyclic voltammetry and UV-vis expts. They reversibly
switch among the entire visible spectra, which is of particular
importance for display applications. Moreover, the EDOT-based
copolymers strongly absorb in the NIR window (1200 nm up to 3000 nm)
with some potential electrochromic applications related to this

Truong 10/728, 088

Page 22

spectral window. Light-emitting diodes were fabricated using these
copolymers as active layer. To improve hole and electron injection,
the active layer was sandwiched between a

ITO/PEDOT:PSSA/copolymer/Ba/Al. The emitting properties were
studied on the base of photoluminescence (PL) and

electroluminescence (EL) expts. The spectral emission varies from
blue-green to yellow, depending on the compn. of the copolymers.
IT 174508-31-7P

(monomer; prepn. and optical properties of and LEDs from
copolymers prepd. from dibromoethylenedioxythiophene or
dibromopyridine and contg. fluorene or. phenylene units)
RN 174508-31-7 HCA

CN Thieno[3,4-b]-l,4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

Br

IT Polymers, preparation

(conjugated; prepn. and optical properties of and LEDs from
copolymers prepd. from dibromoethylenedioxythiophene or
dibromopyridine and contg. fluorene or phenylene units)

IT Doping

(electrochem. ; prepn. and optical properties of and LEDs from
copolymers prepd. from dibromoethylenedioxythiophene or
dibromopyridine and contg. fluorene or phenylene units)

IT Conduction electrons

(injection; prepn. and optical properties of and LEDs from
copolymers prepd. from dibromoethylenedioxythiophene or
dibromopyridine and contg. fluorene or phenylene units)

IT Band gap

(optical; prepn, and optical properties of and LEDs from
copolymers prepd. from dibromoethylenedioxythiophene or
dibromopyridine and contg. fluorene or phenylene units)
IT Band gap

Elect rochromism

Electroluminescent devices

Electronic structure

Glass substrates

Glass transition temperature

HOMO (molecular orbital)

IR spectra

Truong 10/728,088 Page 23

LUMO (molecular orbital)
Luminescence

Luminescence, electroluminescence

Polymerization

Polymerization catalysts

Raman spectra

Redox potential

Redox reaction

Thermal stability

UV and visible spectra

(prepn. and optical properties of and LEDs from copolymers prepd.

from dibromoethylenedioxythiophene or dibromopyridine and contg.

fluorene or phenylene units)
IT 9003-53-6D, sulfonated

(PSS; prepn. and optical properties of and LEDs from copolymers

prepd. from dibromoethylenedioxythiophene or dibromopyridine and

contg. fluorene or phenylene units)
IT 7429-90-5, Aluminum, uses 7440-39-3, Barium, uses

(electrode; prepn. and optical properties of and LEDs from

copolymers prepd. from dibromoethylenedioxythiophene or

dibromopyridine and contg. fluorene or phenylene units)
IT 67399-94-4P, 1, 4-Dioctyloxybenzene 1238 63-99-OP,

9, 9-Dioctylfluorene 156028-40-9P, 1, 4-Dibromo-2, 5-
dioctyloxybenzene 198964-46-4P, 2, 7-Dibromo-9, 9-dioctylf luorene

(intermediate in monomer prepn.; prepn. and optical properties of

and LEDs from copolymers prepd. from

dibromoethylenedioxythiophene or dibromopyridine and contg.

fluorene or phenylene units)
IT 174508-31-7P 19 62 07-58- 6P 4 0 64 61-51- 6P 4 57 931-2 6- 9P

(monomer; prepn. and optical properties of and LEDs from

copolymers prepd. from dibromoethylenedioxythiophene or

dibromopyridine and contg. fluorene or phenylene units)
IT 14221-01-3, Pd(PPh3)4

(polymn. catalysts; prepn. and optical properties of and LEDs

from copolymers prepd. from dibromoethylenedioxythiophene or

dibromopyridine and contg. fluorene or phenylene units)
IT 50926-11-9, ITO 126213-51-2, PEDOT

(prepn. and optical properties of and LEDs from copolymers prepd.

from dibromoethylenedioxythiophene or dibromopyridine and contg.

fluorene or phenylene units)
IT 2 8792 4 -59- BP 2 87 92 4-60-lP 294 637-16-4P 47 3 914-2 1-5P
633290-7 6-3P 71637 7-30-9P 71 6377-3 1-OP 716377-32-lP
716377-33-2P 716377-34-3P

(prepn. and optical properties of and LEDs from copolymers prepd.

from dibromoethylenedioxythiophene or dibromopyridine and contg.

fluorene or phenylene units)
IT 86-73-7, Fluorene 111-83-1, Octyl bromide 123-31-9,

Hydroquinone, reactions 61676-62-8, 2-Isopropoxy-4, 4, 5, 5-

Truong 10/728, 088

Page 24

tetramethyl- [1, 3, 2]dioxaborolane 126213-50-1

(reactant in monomer prepn.; prepn. and optical properties of and
LEDs from copolymers prepd. from dibromoethylenedioxythiophene or
dibromopyridine and contg. fluorene or phenylene units)

L27 ANSWER 4 OF 26 HCA COPYRIGHT 2005 ACS on STN

141:39122 Synthetic methodology toward new propylenedioxythiophene

polymers. Reeves, Benjamin D./ Grenier, Christophe R. G.; Argun,
Avni A.; Cirpan, Ali; Cunningham, Garry B.; McCarley, Tracy D.;
Reynolds, John R. (Department of Chemistry, Center for
Macromolecular Science and Engineering, University of Florida,
Gainesville, FL, 32 611, USA) . Polymer Preprints (American Chemical
Society, Division of Polymer Chemistry), 45(1), 284 (English) 2004.
CODEN; ACPPAY, ISSN: 0032-3934, Publisher: American Chemical
Society, Division of Polymer Chemistry.

AB An extensive family of dioxythiophene-based monomers by Williamson
etherif ication, transetherif ication, and Mitsunobu chem. has been
successfully synthesized by our group, however, the routes developed
are not efficient when synthesizing monomers with large
substituents . Therefore, a new synthetic methodol. has been
employed to access monomers with large nonpolar derivs. First,
3, 4-dimethoxythiophene is subject to a transetherif ication reaction
with 2, 2-bis (bromomethyl) -1, 3-propanediol. The bromomethyl
derivatized ProDOT then undergoes a Williamson etherif ication with
octadecanol and the octadecyl deriv. was then brominated with NBS
followed by polymn. by Grignard metathesis. The resulting polymer
after purifn. by fractionation was characterized by NMR, GPC,
MALDI-TOF, X-ray powder diffraction, DSC, and TGA. The polymer was
highly sol. in org. solvents, which allowed the spray casting of
thin films from soln. and the films were then electrochromically
characterized and incorporated into dual polymer electrochromic
devices. Also, a polymer soln. in toluene gave a relatively high
fluorescence quantum efficiency with a value of 0.40.

IT 700817-10-3P

(synthesis of propylenedioxythiophene-based monomer for polymers
thereof)

RN 700817-10-3 HCA

CN 2H-Thieno [3, 4-b] [1, 4] dioxepin, 6, 8-dibromo-3, 4-dihydro-3, 3-
bis [ (octadecyloxy) methyl ] - (9CI) (CA INDEX NAME)

Me- (CH2) 17-0-CH2 ^ — q

Truong 10/728, 088

Page 25

IT Polymerization

(Grignard; synthesis of propylenedioxythiophene polymers and

fluorescence thereof)
IT Alkoxylation

(Williamson; synthesis of propylenedioxythiophene-based monomer

for polymers thereof)
IT Polymerization

(metathetic; synthesis of propylenedioxythiophene polymers and

fluorescence thereof)
IT Fluorescence

(of propylenedioxythiophene polymers)
IT Conducting polymers

(polythiophenes; synthesis of propylenedioxythiophene polymers

and fluorescence thereof)
IT Etherif ication

(transetherif ication; synthesis of propylenedioxythiophene-based
monomer for polymers thereof)
IT 3296-90-0 51792-34-8

(in synthesis of propylenedioxythiophene-based monomer for
polymers thereof)
IT 634591-77-8P 701209-98-5P

(in synthesis of propylenedioxythiophene-based monomer for
polymers thereof)
IT 700817-18-lP

(synthesis of propylenedioxythiophene polymers and fluorescence

thereof)
IT 700817-10-3P

(synthesis of propylenedioxythiophene-based monomer for polymers

thereof)

L27 ANSWER 5 OF 26 HCA COPYRIGHT 2005 ACS on STN

141:24056 Solution processable and electrochromic dioxythiophene-based
polymers. Reeves, Benjamin D.; Grenier, Christophe R. G.; Argun,
Avni A.; Cirpan, Ali; McCarley, Tracy D.; Reynolds, John R.
(Department of Chemistry, Center for Macromolecular Science and
Engineering, University of Florida, Gainesville, FL, 32611, USA) .
Polymer Preprints (American Chemical Society, Division of Polymer
Chemistry), 45(1), 180 (English) 2004. CODEN: ACPPAY. ISSN: .
0032-3934, Publisher: American Chemical Society, Division of
Polymer Chemistry.

AB This work presents the development of a family of sol. processable
disubstituted propylenedioxythiophenes and an anal, of their
electrochromic properties. 2,5-Dibromo derivatized dioxythiophene
monomers underwent Grignard metathesis polymn. to afford org. sol.
neutral polymers. Polymers were characterized by NMR, GPC,
MALDI-TOF, X-ray powder diffraction, TGA, and DSC. Mol. wt .
characterization by GPC vs. polystyrene stds. indicated no. av. mol.

Truong 10/728,088

Page 26

IT

RN
CN

wts. between 7-40 kg/mol. MALDI-TOF studies were performed which
gave a set of dominant peaks sepd. by 322 amu, corresponding to the
mol. wt. of the monomer repeat unit. Thin films were processed by
spray casting polymer solns. onto a working electrode.
Spectroelectrochem. , colorimetry, and composite coloration
efficiencies studies show that the spray cast polymers have the same
contrast ratio and switching speeds as the electrodeposited films of
the same thickness. The composite coloration efficiency values for
this family are two to three times larger than previously obsd. for
electrodeposited dioxythiophene polymers.
700817-04-5P 700817-06-7P 700817-08-9P
700817-10-3P

(monomer; in prepn. of soln. processable and electrochromic
dioxythiophene-based polymers)
700817-04-5 HCA

2H-Thieno[3, 4-b] [1, 4] dioxepin, 6, 8-dibromo-3, 3-dihexyl-3, 4-dihydro-
(9CI) (CA INDEX NAME)

Me- (CH2) 5
Me- (CH2)5

RN 700817-06-7 HCA

CN 2H-Thieno[3, 4-b] [ 1, 4 ] dioxepin, 6, 8-dibromo-3, 3-bis {2-ethylhexyl) -3, 4-
dihydro- (9CI) (CA INDEX NAME)

RN 700817-08-9 HCA ^

CN 2H-Thieno [3, 4-b] [1, 4] dioxepin, 6, 8-dibromo-3, 3-bis [ [ (2-

ethylhexyl) oxy] methyl] -3, 4-dihydro- (9CI) (CA INDEX NAME)

Truong 10/728, 088

Page

RN 700817-10-3 HCA

CN 2H-Thieno [3, 4-b] [ 1 , 4 ] dioxepin, 6, 8-dibromo-3, 4-dihydro-3/3-
bis[ (octadecyloxy) methyl]- (9CI) (CA INDEX NAME)

Me- (CH2) 17~0-CH2

Me- (CH2) 17-0-CH2

IT Alkoxylation

(Williamson; in prepn. of monomers for soln. processable and

electrochromic dioxythiophene-based polymers)
IT Bromination

Transesterif ication

(in prepn. of monomers for soln. processable and electrochromic

dioxythiophene-based polymers)
IT Polymerization

(metathetic; in prepn. of soln. processable and electrochromic

dioxythiophene-based polymers)
IT Optical switching

(of electrochromic dioxythiophene-based polymers)
IT Molecular weight

(of soln. processable and electrochromic dioxythiophene-based
polymers)
IT Conducting polymers

(polythiophenes; prepn. of soln. processable and electrochromic
dioxythiophene-based polymers)
IT Electrochromic materials

(prepn. of soln. processable and dioxythiophene-based polymers

for electrochromic materials)
IT 128-08-5, N-Bromosuccinimide

Truong 10/728, 088

Page 28

(in prepn. of monomers for soln. processable and electrochromic

dioxythiophene-based polymers)
IT 51792-34-8, 3, 4-Dimethoxythiophene 54662-33-8 57355-20-1
7 00816-90-6 7 00816-93-9

(in prepn. of soln. processable and electrochromic

dioxythiophene-based polymers)
IT 634591-75- 6P 634 591-77-8P 70081 6-98-4P 7 0 08 17- 00- IP

(in prepn. of soln. processable and electrochromic

dioxythiophene-based polymers)
IT 700817-04-5P 700817-06-7P 700817-08-9P
700817-10-3P

(monomer; in prepn. of soln. processable and electrochromic
dioxythiophene-based polymers)
IT 700817-12-5P 700817- 14 -7P 7 00817-1 6- 9P 7 008 17-1 8- IP
(prepn. of soln. processable and electrochromic
dioxythiophene-based polymers)

L27 ANSWER 6 OF 26 HCA COPYRIGHT 2005 ACS on STN

140:77531 Solid-State Synthesis of a Conducting Polythiophene via an
Unprecedented Heterocyclic Coupling Reaction. Meng, Hong;
Perepichka, Dmitrii F.; Bendikov, Michael; Wudl, Fred; Pan, Grant
Z.; Yu, Wenjiang; Dong, Wenjian; Brown, Stuart (Department of
Chemistry and Biochemistry and the Exotic Materials Institute,
Microf abrication Lab, Department of Physics and Astrophysics,
University of California, Los Angeles, CA, 90095-1569, USA) .
Journal of the American Chemical Society, 125(49), 15151-15162
(English) 2003. CODEN: JACSAT. ISSN: 0002-7863. Publisher:
American Chemical Society.

AB Prolonged storage (.apprx.2 yr) or gentle heating (50-80 °C)

of cryst. 2, 5-dibromo-3, 4-ethylenedioxythiophene (DBEDOT) affords a
highly conducting, bromine-doped poly (3, 4-ethylenedioxythiophene)
(PEDOT), as confirmed by solid-state NMR, FTIR, CV, and vis-NIR
spectroscopies. The novel solid-state polymn. (SSP) does not occur
for 2, 5-dichloro-3, 4-ethylenedioxythiophene (DCEDOT) , and requires a
much higher temp. (>130 °C) for 2, 5-diiodo-3, 4-

ethylenedioxythiophene (DIEDOT) . X-ray structural anal, of the
above dihalothiophenes reveals short Hal- • -Hal

distances- between adjacent mols. in DBEDOT and DIEDOT, but not in
DCEDOT. The polymn. may also occur in the melt but is significantly
slower and leads to poorly conductive material. Detailed studies of
the reaction were performed using ESR, DSC, microscopy, and
gravimetric analyses. SSP starts on crystal defect sites; it is
exothermic by 14 kcal/mol and requires activation energy of
.apprx.2 6 kcal/mol (for DBEDOT) . The temp, dependence of the cond.
of SSPtPEDOT (art = 20-80 S/cm) reveals a slight thermal
activation. It can be further increased by a factor of 2 by doping
with iodine. Using this approach, thin films of PEDOT with cond. as
high as 20 S/cm were fabricated on insulating flexible plastic

Truong 10/728,088

Page 29

surfaces.

IT 225518-49-OP, 2 , 5-Dichloro-3, 4-Ethylenedioxythiophene
640737-72-OP

(solid-state synthesis of conducting polythiophenes via
unprecedented heterocyclic coupling reaction)

RN. 225518-49-0 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dichloro-2, 3-dihydro- (9CI) (CA INDEX
NAME)

CI

RN 640737-72-0 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 2, 3-dihydro-5, 7-diiodo- {9CI) (CA INDEX
NAME)

IT 174508-31-7P, 2, 5-Dibromo-3, 4-Ethylenedioxythiophene

(solid-state synthesis of conducting polythiophenes via
unprecedented heterocyclic coupling reaction)
RN 174508-31-7 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

Br

IT NMR spectroscopy

(carbon-13, solid state; solid-state synthesis of conducting

Truong 10/728, 088

Page 30

polythiophenes via unprecedented heterocyclic coupling reaction)
IT Polymer morphology

(cryst.; solid-state synthesis of conducting polythiophenes via

unprecedented heterocyclic coupling reaction)
IT Conducting polymers

(polythiophenes; solid-state synthesis of conducting

polythiophenes via unprecedented heterocyclic coupling reaction)
IT Electric conductivity

(solid-state synthesis of conducting polythiophenes via

unprecedented heterocyclic coupling reaction)
IT 225518-49-OP, 2, '5-Dichloro-3, 4-Ethylenedioxythiophene
640737-72-OP

(solid-state synthesis of conducting polythiophenes via

unprecedented heterocyclic coupling reaction)
IT 350037-71-7P, 2, 5-Dibromo-3, 4-Ethylenedioxythiophene homopolymer

(solid-state synthesis of conducting polythiophenes via

unprecedented heterocyclic coupling reaction)
IT 174508-31-7P, 2, 5-Dibromo-3, 4-Ethylenedioxythiophene
640737-73-lP

(solid-state synthesis of conducting polythiophenes via

unprecedented heterocyclic coupling reaction)
IT 109-72-8, n-Butyl lithium, reactions 128-08-5, N-Bromosuccinimide
128-09-6, N-Chlorosuccinimide 1600-27-7, Mercuric acetate
7553-56-2, Iodine, reactions 126213-50-1, 3,4-
Ethylenedioxythiophene

(solid-state synthesis of conducting polythiophenes via

unprecedented heterocyclic coupling reaction)

L27 ANSWER 7 OF 2 6 HCA COPYRIGHT 2005 ACS on STN

139:149947 Stable and Soluble Oligo (3, 4-ethylenedioxythiophene) s

End-Capped with Alkyl Chains. Turbiez, Mathieu; Frere, Pierre;

Roncali, Jean (Groupe Systemes Conjugues Lineaires, Laboratoire

IMMO, UMR CNRS 6501, Universite d'Angers, Angers, 49000, Fr,).

Journal of Organic Chemistry, 68(13), 5357-5360 (English) 2003.

CODEN: JOCEAH. ISSN: 0022-3263. Publisher: American Chemical

Society.

AB The synthesis of a new series of stable and sol. EDOT oligomers
end-capped with n-hexyl groups is described. Optical and
electrochem. results indicate that the synergy between the direct
electron-releasing effects of the ethylenedioxy groups and the
self-rigidif ication resulting from intramol. interactions controls
to a large extent the HOMO-LUMO gap.

IT 174508-31-7P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene
(intermediate; prepn. of, and in reaction with
tributylstannylhexyl-EDOT)

RN 174508-31-7 HCA

CN Thieno[3,4-b]-l,4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

4

Truong 10/728,088

Page 31

Br

0.

^0'

Br

IT UV absorption

(UV-visible; of oligo (3, 4-ethyleneciioxythiophene) s end-capped
with alkyl chains)
IT Bathochromic effect
Crystal structure
Cyclic voltammetry
Oxidation potential
Solubility

(of oligo (3, 4-ethylenedioxythiophene) s end-capped with alkyl

chains)
IT 569665-35-6P

(dimer; synthesis and properties of oligo(3,4-

ethylenedioxythiophene) s end-capped with alkyl chains)
IT 128-08-5, NBS

(in reaction with EDOT or bisEDOT)
IT 126213-50-1, 3, 4-Ethylenedioxythiophene

(in reaction with bromohexane)
IT 25495-91-4, Bromohexane

(in reaction with ethylenedioxythiophene or

bis ethyl enedioxythiophene)
IT 1461-22-9, Tributylstannyl chloride

(in reaction with hexylethylenedioxythiophene)
IT 569665-37-8P

(intermediate; prepn. of, and in reaction with dibromo-EDOT or

dibromo-bisEDOT )
IT 569665-30-lP

(intermediate; prepn. of, and in reaction with tributylstannyl

chloride or in dimerization)
IT 174508-31-7?, 2, 5-Dibromo-3, 4-ethylenedioxythiophene
287924-56-5P

(intermediate; prepn. of, and in reaction with

tributylstannylhexyl-EDOT)
IT 569665-32-3P

(prepn. of)
IT 195602-17-6

(reaction with bromohexane in synthesis of dimer)
IT 569665-42-5P

(tetramer; synthesis and properties of oligo(3,4-

r

Truong 10/728, 088

Page 32

ethylenedioxythiophene) s end-capped with alkyl chains)
IT 569665-39-OP

(trimer; synthesis and properties of oligo(3,4~
ethylenedioxythiophene) s end-capped with alkyl chains)

L27 ANSWER 8 OF 2 6 HCA COPYRIGHT 2005 ACS on STN

138 : 304877 3, 4-Ethylenedioxy-substituted bithiophene-alt-thiophene-S, S-
dioxide regular copolymers. Synthesis and conductive, magnetic and
luminescence properties.. Berlin, Anna; Zotti, Gianni; Zecchin,
Sandro; Schiavon, Gilberto; Cocchi, Massimo; Virgili, Dalia;
Sabatini, Cristiana (Istituto CNR di Scienze e Tecnologie
Molecolari, Milan, 20133, Italy) . Journal of Materials Chemistry,
13(1), 27-33 (English) 2003. CODEN: JMACEP. ISSN: 0959-9428.
Publisher: Royal Society of Chemistry.

AB Polyconjugated regular bithiophene-alt-thiophene-S, S-dioxide
copolymers were produced by anodic coupling of variously
3, 4-ethylenedioxy-substituted 2, 5-bis (2-thienyl) thiophene-S, S-
dioxide. The polymers were characterized by cyclic voltammetry,
FTIR reflection-absorption and UV-vis spectroscopy, MALDI-TOF mass
spectroscopy, electrochem. quartz crystal microbalance, in situ ESR
. and in situ cond. techniques, photo- and electro-luminescence
measurements. The regular alternation of electron-rich and -poor
thiophene rings in the polymer chain operated by the ethylenedioxy
and S,S-dioxide moieties produces a finite window of cond.
Alkyl-protection of the p-positions of the thiophene-S, S-
dioxide ring gave low-defect and sol. oligomers which were
investigated in single-layer org. light-emitting devices (OLEDs) .
Photoluminescence quantum efficiency of .apprx.1% and external
electroluminescence quantum efficiencies of 0.01% photon/electron at
a luminance of 100 cd m-2 were obtained.

IT 174508-31-7, 2, 5-Dibromo-3, 4- (ethylenedioxy) thiophene

RN 174508-31-7 HCA

CN Thieno[3,4-b]-l,4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

(oxidn. of)

Br

Br

IT 511286-87-6P

(prepn. and reaction with (tributylstannyl) thiophene)
RN 511286-87-6 HCA

Truong 10/728,088

Page 33

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-ciibroino-2, 3-dihydro-, 6, 6-dioxide
(9CI) (CA INDEX NAME)

IT Oxidation potential
Reduction potential

(of ethylenedioxy-substituted bis (thienyl) thiophene dioxide
monomers and polymers)
IT Electric conductivity
Luminescence

Luminescence, electroluminescence

(prepn, and conductive, magnetic and luminescence properties of

ethylenedioxy-substituted bithiophene-alt-thiophene dioxide

polymers)
IT Electroluminescent devices

(single-layer electroluminescence devices prepd. from

ethylenedioxy-substituted bithiophene-alt-thiophene dioxide

polymers)
IT Polycarbonates, properties

(single-layer electroluminescence devices prepd. from

ethylenedioxy-substituted bithiophene-alt-thiophene dioxide

polymers and)
IT 25037-45-0, Bisphenol A polycarbonate

(assumed monomers; single-layer electroluminescence devices

prepd. from ethylenedioxy-substituted bithiophene-alt-thiophene

dioxide polymers and)
IT 174508-31-7, 2, 5-Dibromo-3, 4- (ethylenedioxy) thiophene
174509-52-5

(oxidn. of)

IT 51128 6-88-7P 51128 6-89-8P 511286-90-lP 5112 86-91-2P
511286-92-3P

(prepn. and conductive, magnetic and luminescence properties of)
IT 51128 6-81-OP 51128 6-82-lP 511286-83-2P 51128 6-84-3P
511286-85-4P

(prepn. and polymn, of)
IT 511286-86-5P

(prepn. and reaction with (tributylstannyl) (ethylenedioxy) thiophe

ne)

IT 511286-87-6P

(prepn. and reaction with (tributylstannyl) thiophene)

Truong 10/728, 088

Page 34

IT 89088-95-9, 2, 5-Dibroraothiophene-l, 1-dioxide

(reaction with (tributylstannyl) (ethylenedioxy) thiophene)

IT 175922-79-9, 2- (Tributylstannyl) -3, 4- (ethylenedioxy) thiophene
(reaction with dibromothiophene dioxide)

IT 24936-68-3, Bisphenol A polycarbonate, sru, properties 65181-78-4,
N, N' -Diphenyl-N,N* -bis ( 3-methylphenyl ) -1, 1 ' -biphenyl-4 , 4 ' -diamine
(single-layer electroluminescence devices prepd. from
ethylenedioxy-substituted bithiophene-alt-thiophene dioxide
polymers and)

L27 ANSWER 9 OF 26 HCA COPYRIGHT 2005 ACS on STN

138:288055 Facile solid-state synthesis of highly conducting

poly (ethylenedioxythiophene) . Meng, Hong; Perepichka, Dmitrii F.;
Wudl, Fred (Department of Chemistry and Biochemistry and Exotic
Materials Institute, University of California, Los Angeles, CA,
90095-1569, USA). Angewandte Chemie, International Edition, 42(6),
658-661 (English) 2003. CODEN: ACIEF5. ISSN: 1433-7851.
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA.

AB The prepn. of PEDOT by catalyst-free coupling polymn. of

2, 5-dibromo-3, 4-ethylenedioxythiophene in the solid state at
accelerated temps. (60, 80, and 120°) is reported. The cond.
of polymer films on plastic and glass substrate was examd. Crystal
structure data for the monomer are presented.

IT 174508-31-7, 2, 5-Dibromo-3, 4-ethylenedioxythiophene
(structure and solid-state polymn. of
dibromoethylenedioxythiophene )

RN 174508-31-7 HCA

CN Thieno[3,4-b]-l,4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

Br

Br

IT Polymer morphology

(cryst.; solid-state polymn. of dibromoethylenedioxythiophene and

cond. of poly (ethylenedioxythiophene) )
IT Crystal structure

(of 2, 5-dibromo-3, 4-ethylenedioxythiophene)
IT Conducting polymers

Electric conductivity

(solid-state polymn. of dibromoethylenedioxythiophene and cond.

of poly (ethylenedioxythiophene) )

Truong 10/728, 088

Page 35

IT 163359-60-2P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene homopolymer ,
SRU 350037-71-7P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene
homopolymer

(solid-state polymn. of dibromoethylenedioxythiophene and cond.
of poly (ethylenedioxythiophene) )
IT 174508-31-7, 2, 5-Dibromo-3, 4-ethylenedioxythiophene
(structure and solid-state polymn. of
dibromoethylenedioxythiophene)

L27 ANSWER 10 OF 26 HCA COPYRIGHT 2005 ACS on STN

138:188206 EQCM analysis of the alkali metal ion coordination properties
of novel poly ( thiophene) s 3, 4-functionalized with crown-ether
moieties. Berlin, A.; Zotti, G.; Zecchin, S.; Schiavon, G.
(Istituto CNR di Scienze e Tecnologie Molecolari, Milan, 20133,
Italy). Synthetic Metals, 131(1-3), 149-160 (English) 2002. CODEN:
SYMEDZ. ISSN: 0379-6779. Publisher: Elsevier Science B.V,.

AB New thiophenes carrying 18-crown-6-ether ring directly linked to the
3- and 4-positions of the thiophene ring were synthesized and
polymd. by anodic coupling in acetonitrile . The polymers were
characterized by cyclic voltammetry (CV) , UV-Vis and FTIR
spectroscopy, matrix-assisted laser desorption ionization (MALDI)
mass spectroscopy and in situ cond. Electrochem. quartz crystal
microbalance (EQCM) anal, of the alkali metal coordination ability
of the 18-crown-6-ether polymer films in acetonitrile has evidenced
that the coordination consts. (e.g. 20-80 M-1 for Na+) are ca. two
orders of magnitude lower than those of polythicphenes bearing the
crown substituents pendant from the polythiophene backbone. The
result has been ascribed both to electronic and solid-state effects
of the conjugated polythiophene chains.

IT 233756-39-3P

(EQCM anal, of alkali metal ion coordination properties of
poly (thiophene) s 3 , 4-functionalized with crown-ether moieties)

RN 233756-39-3 HCA

CN Thieno [3,4-b]-l,4,7,10,13, 1 6-hexaoxacyclooctadecin,

17, 19-dibromo-2, 3, 5, 6, 8, 9, 11, 12 , 14 , 15-decahydro- (9CI) (CA INDEX
NAME)

IT Cyclic voltammetry

Electric conductivity

Truong 10/728, 088

Page 36

(EQCM anal, of alkali metal ion coordination properties of
poly (thiophene) s 3, 4-f unctionalized with crown-ether moieties)

IT Polymerization

(electrochem. ; EQCM anal, of alkali metal ion coordination
properties of poly (thiophene) s 3, 4-functionalized with
crown-ether moieties)

IT 7439-93-2, Lithium, properties 7440-23-5, Sodium, properties
(EQCM anal, of alkali metal ion coordination properties of
poly (thiophene) s 3, 4-functionalized with crown-ether moieties)

IT 24 9513-23-3P 484 640-50-8P 484 640-51-9P 497937-33-4P
497937-34-5P

(EQCM anal, of alkali metal ion coordination properties of
poly (thiophene) s 3, 4-functionalized with crown-ether moieties)
IT 122372-75-2 12 6213-50-1 4 84 64 0-4 8-4 4 84 640-4 9-5

(EQCM anal, of alkali metal ion coordination properties of
poly (thiophene) s 3, 4-functionalized with crown-ether moieties)
IT 233756-39-3P 497937-32-3P

(EQCM anal, of alkali metal ion coordination properties of
poly (thiophene) s 3, 4-functionalized with crown-ether moieties)

L27 ANSWER 11 OF 26 HCA COPYRIGHT 2005 ACS on STN

138:178716 Cyano-substituted oligothiophenes : a new approach to n-type
organic semiconductors. Yassar, Abderrahim; Demanze, Frederic;
Jaafari, Abdelhafid; El Idrissi, Mustapha; Coupry, Claude (ITODYS,
Paris, F-75005, Fr.). Advanced Functional Materials, 12(10),
699-708 (English) 2002. CODEN: AFMDC6. ISSN: 1616-301X.
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA.

AB A series of a,co-cyano oligothiophenes with three to six
rings, as well as seven p, p ' -substituted cyano

terthiophenes have been synthesized using a palladium-catalyzed
coupling reaction via organotin or organozinc intermediates. The
structure of an oligothiophene trimer has been detd. by X-ray
crystallog.; its space group is monoclinic (C2/c) with four mols.
per unit cell (Z = 4) . The mols. adopt the n-n stacking
structure. UV-vis spectra of these materials as thin films show a
bathochromic shift compared to unsubstituted oligothiophenes. These
bathochromic shifts are interpreted in the light of charge transfer
exciton. Cyano end-capped sexithiophene (CN-6T-CN) sandwiched
between various metals (metal/CN-6T-CN/metal) , to form Schottky
diode structures, were fabricated by vapor deposition. The electron
injection and rectification ratio strongly depend on the metal
contact, namely the work function of the metal is compatible with
the electron affinity of the org. material. The current-voltage
results are compatible with n-type conduction in CN-6T-CN.

IT 174508-31-7

(prepn. of cyano-substituted oligothiophenes as n-type org.
semiconductors )

RN 174508-31-7 HCA

Truong 10/728,088

Page 37

Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2, 3-dihydro- {9CI) (CA INDEX
NAME)

Exciton

(charge-transfer; prepn, of cyano-substituted oligothiophenes as
n-type org. semiconductors)
Coupling reaction

Crystal structure-property relationship
Electric current-potential relationship
Electron transport

Molecular structure-property relationship
NMR (nuclear magnetic resonance)
Schottky diodes'
Semiconductor materials
UV and visible spectra
Work function

(prepn, of cyano-substituted oligothiophenes as n-type org.
semiconductors )
1461-22-9D, Tr ibutyltin chlori de, derivs.

(Tributyltih; prepn. of cyano-substituted oligothiophenes as
n-type org. semiconductors)
14221-01-3, Tetrakis (triphenylphosphi ne) palladiu m

(prepn. of cyano-substituted oFigothiophenes as n-type org.
semiconductors )

7429-90-5, Aluminum, uses 7440-22-4, Silver, uses 7440-57-5,
Gold, uses " ■

(prepn. of cyano-substituted oligothiophenes as n-type org.

semiconductors )
110230-97-2P 134273-55-5P 17 6787-98-7P 17 6788-00-4P
183069-73-OP 188564-97-8P 188564-98-9P

(prepn. of cyano-substituted oligothiophenes as n-type org.

semiconductors )
241495-53-4P

(prepn. of cyano-substituted oligothiophenes as n-type org.
semiconductors)

109-72-8, reactions 544-92-3, Copper cyanide CuCN 1003-09-4,
2-Bromothiophene 1081-34-1, 2 , 2^T5r'T2'^~^^TETrhiophene 1189-71-5,
N-Chlorosulfonyl isocyanate 1641-09-4 , 3-Cyanothiophene
3141-27-3, 2, 5-Dibromothiophene 3480-11-3, 5-Bromo-2, 2 ' -

Br

Br

Truong 10/728, 088

Page 38

bithiophene 4111-54-0, Lithium diisopropylamide 7646-85-7, Zinc
chloride, reactions 18853-32-2, 3, 4-Dicyanothiophene 94581-95-0,
5-Bromo-2, 2 ' : 5' , 2 ' ' -terthiophene 98057-08-0 174508-31-7
176787-97-6 176787-99-8 497839-26-6 497839-27-7 497839-28-8 '
497839-29-9

(prepn. of cyano-substituted oligothiophenes as n-type org.
semiconductors )
IT 2160-62-5P, 5-Bromo-2-cyanothiophene 1454 83-63-2P,

2, 5-Bis (tributylstannyl) thiophene 171290-94-lP 176787-96-5P
(prepn. of cyano-substituted oligothiophenes as n-type org.
semiconductors )

L27 ANSWER 12 OF 26 HCA COPYRIGHT 2005 ACS on STN
136:200547 Neutral poly ( 3, 4-ethylenedioxythiophene-2, 5-diyl ) s :

preparation by organometallic polycondensation and their unique
p-doping behavior. Yamamoto, Takakazu; Shiraishi, Kouichi; Abla,
Mahmut; Yamaguchi, Isao; Groenendaal, L. "Bert" (Chemical Resources
Laboratory, Tokyo Institute of Technology, Yokohama, Midori-ku,
226-8503, Japan). Polymer, Volume Date 2002, 43(3), 711-719
(English) 2001. CODEN: POLMAG. ISSN: 0032-3861. Publisher:
Elsevier Science Ltd. .
AB Neutral and non-doped poly (3, 4-ethylenedioxythiophene) , PEDOTh(Ni),

rand its hexyl deriv., PED0Th-C6 (Ni) , have been prepd. by
organometallic dehalogenation polycondensation of
2, 5-dichloro-3, 4-ethylenedioxythiophene and its hexyl deriv. with a
zerovalent nickel complex. PED0Th-C6 (Ni) was sol. in org ^ solvent s
and IH NMR data indicated that it had an Mn of 11,000. MALDI-TOF
mass anal, of PEDOTh(Ni) gave Mn and Mw of about 1700 and 2400,
resp. PED0Th-C6 (Ni) showed a UV-Vis absorption peak at 54 6 nm in
CHC13. Electrochem. oxidn. of PED0Th-C6 (Ni ) started at about -0.40
V vs Ag+/Ag and gave a peak at 0.20 V vs Ag+/Ag. Chem. and
electrochem, oxidn. (or p-doping) of PED0Th-C6 (Ni) , both in solns.
and in a solid state, led to weakening of the original tc-tc*
peaks and rise of new peak(s) in a region of 800-1500 nm. The
p-doping of PED0Th-C6 (Ni) caused not only a decrease in the
intensity of IH NMR signals of the bridging ethylene hydrogens but
also a decrease in that of the hexyl side chain, suggesting a strong
\ interaction of the p-dopant with the side chain. NMR data of

poly (3-methoxythiophene-2, 5-diyl) also supported an assumption that
p-doping brings about a severe change in electronic state of the
substituent attached to the polythiophene main chain. PEDOTh(Ni)
had a d. of 1.71 g cm-3; the mol. packing mode of PEDOTh(Ni) is
discussed based on the d. of the polymer and its XRD data.
IT 225518-49-OP 350827-42-8P

(prepn. of neutral poly (ethylenedioxythiophenediyl ) s by
organometallic polycondensation and their unique p-doping
behavior)
RN 225518-49-0 HCA

Truong 10/728,088

Page 39

CN Thieno[3,4-b]-l,4-dioxin, 5, 7-dichloro-2 , S-dihydro- (9CI) (CA INDEX
NAME)

CI

CI

RN 350827-42-8 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dichloro-2-hexyl-2 , 3-dihydro- (9CI)
(CA INDEX NAME)

CI

Me-(CH2)5 O^^JL

O

CI

IT Electric conductivity

(prepn. of neutral poly (ethylenedioxythi
organometallic polycondensation and thei
behavior)

IT 163359-60-2P 225518-50-3F 350827-43-9P
(prepn. of neutral poly (ethylenedioxythi
organometallic polycondensation and thei
behavior)

IT 12 6213-50-1 12 6213-53-4

(prepn. of neutral poly (ethylenedioxythi
organometallic polycondensation and thei
behavior)

IT 225518-49-OP 350827-42-8P

(prepn. of neutral poly (ethylenedioxythi
organometallic polycondensation and thei
behavior)

ophenediyl)s by
r unique p-doping

351317-30-lP

ophenediyl ) s by
r unique p-doping

ophenediyl) s by
r unique p-doping

ophenediyl) s by
r unique p-doping

L27 ANSWER 13 OF 26 HCA COPYRIGHT 2005 ACS on STN
135:242592 Optical and electrochemical properties of soluble

N-hexylcarbazole-co-3, 4-ethylenedioxythiophene copolymers . Beouch,
L.; Tran Van, F. ; Stephan, 0.; Vial, J. C; Chevrot, C. (Equipe
Reactivite aux Interfaces (EA 2528), Laboratoire sur les Polymeres
et les Materiaux Electroactif s, Universite de Cergy Pontoise, Cergy

Truong 10/728,088

Page 40

Pontoise, 95013, Fr.). Synthetic Metals, 122(2), 351-358 (English)
2001. CODEN: SYMEDZ . ISSN: 0379-6779. Publisher: Elsevier Science
3 • • •

AB Sol . N-hexylcarbazole-co-3, 4-ethylenedioxythiophene (HCz-co-EDOT)
copolymers from mixts. in various ratio of the two corresponding
dihalogenated monomers were synthesized. The random copolymers were
obtained from EDOT/HCz starting molar ratio: 0.25, 1, 4, named,
resp., CI, C2 and C3, and compared their properties to the two
homopolymers synthesized in the same way. The IR studies clearly
indicated, that an increase in the amt . of ethylenedioxythiophene in
the feed compn. leads to an increase of the proportion of the
corresponding comonomer in the final materials. Elemental anal,
point out that the reactivity of dibrominated EDOT seems slightly
lower than that of dibrominated HCz. Thin films of copolymer have
been prepd. and their electrochem. response have been investigated.
Absorption and luminescence of these materials have been also
studied in CHC13. Copolymers mainly composed of one monomer (CI and
C3) behaves like the corresponding homopolymers. On an other hand,
copolymer (02) obtained from an equimolar amt. of each monomer in
the feed compn. clearly exhibits distinct signals in optical spectra
and in electrochem. behavior, probably due to the presence of each
monomer unit short segments . The use of C2 has been explored for
possible application in light emitting devices indicating that the
p-doping of the material would be facilitated leading to an improved
hole injecting when compared to carbazole homopolymer. It could be
particularly interesting as a hole transporting layer in multilayer
org. light emitting devices,

IT 174508-31-7P

(optical and electrochem. properties of sol. N-hexylcarbazole-co-
3, 4-ethylenedioxythiophene copolymers)

RN 174508-31-7 HCA

ON Thieno[3,4-b]-l,4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

IT Absorption spectra
Cyclic voltammetry
Fluorescence
Hole transport
Luminescence

Truong 10/728,088

Page 41

Luminescence, electroluminescence

(optical and elect«rochem, properties of sol. N-hexylcarbazole-co-
3, 4-ethylenedioxythiophene copolymers)
IT Band gap

(optical; optical ^nd electrochem. properties of sol.

N-hexylcarbazole-co^S, 4-ethylenedioxythiophene copolymers)
IT Polymers, preparation ^

(polythiophenes, carbazole group-contg . ; optical and electrochem.

properties of sol. NThexylcarbazole-co-3, 4-ethylenedioxythiophene

copolymers) \
IT 7440-66-6, Zinc, uses \

(activated; optical and electrochem. properties of sol.

N-hexylcarbazole-co-3,^^-ethylenedioxythiophene copolymers)
IT 56-37-1, Triethylbenzylammonium chloride

(optical and electrocheV. properties of sol. N-hexylcarbazole-co-

3, 4-ethylenedioxythiophene copolymers)
IT 1 63359- 60-2P 350 037-7 1-7R 359829- 15-5P 359829-1 6- 6P
359829-17-7P, Poly ( 9-hexyl-9H-carbazole-3, 6-diyl)

(optical and electrochem^ properties of sol. N-hexylcarbazole-co-

3, 4-ethylenedioxythiopherl'^e copolymers)
IT 111-25-1, Hexyl bromide 128-08-5, N-Bromosuccinimide 6825-20-3,
3, 6-Dibromocarbazole 126213-50-1, 3, 4-Ethylenedioxythiophene

(optical and electrochem. properties of sol. N-hexylcarbazole-co-

3, 4-ethylenedioxythiophene\ copolymers)
IT 150623-72-6P 174508-31-7P \

(optical and electrochem. properties of sol. N-hexylcarbazole-co-

3, 4-ethylenedioxythiophene popolymers)
IT 46389-47-3, 2,2' -Bip yr idinenickel dibromi de

(polymn. catalyst; optical and electr^ochem. properties of sol.

N-hexylcarbazole-co-3, 4-ethylenedioxythiophene copolymers)

L27 ANSWER 14 OF 26 HCA COPYRIGHT 2005 ACS on STN
135:122840 Preparation of a soluble and neutral alkyl derivative of
poly (3, 4-ethylene-dioxythiophene) and its optical properties.
Shiraishi, K.; Kanbara, T.; Yamamoto, T.; Groenendaal, L. B.
(Chemical Resources Laboratory, Tokyo Institute of Technology,
Nagatsuta, Midori-ku, Yokohama, 226-8503, Japan). Polymer, 42(16),
7229-7232 (English) 2001. CODEN: POLMAG. ISSN: 0032-3861.
Publisher: Elsevier Science Ltd. .
AB Sol. and non-doped poly (3, 4-ethylenedioxythiophene) with a hexyl

substituent (PED0Th-C6 (Ni) ) , was first synthesized by Ni promoted
dehalogenation polycondensation of the corresponding monomer.
PED0Th-C6 (Ni) exhibited good soly. in common org. solvents such as
QHC13, CH2C12, and DMF, in contrast to poor soly. of the
corresponding polymer synthesized by oxidative polymn. GPC anal,
indicated that PED0Th-C6 (Ni) had Mn and Mw of 5400 and 8500 (vs
polystyrene stds.); IH NMR anal, gave an Mn value of 11,000. A cast
film of PED0Th-C6 (Ni) received electrochem. p-doping at 0.20 V vs

\

Truong 10/728, 088

Page 42

Ag+/Ag. Chem. and electrochem. oxidn. of PED0Th-C6 (Ni) led to
appearance of new absorption bands in the near IR region.
IT 350827-42-8P

(monomer; prepn, of a sol. and neutral hexyl deriv. of
poly (3, 4-ethylene-dioxythiophene) and optical properties of
riondoped and doped polymers)
RN 350827-42-8 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dichloro-2-hexyl-2, 3-dihydro- (9CI)
(CA INDEX NAME)

IT Dopants

Doping

UV and visible spectra

(prepn, of a sol. and neutral hexyl deriv. of
poly (3, 4-ethylene-dioxythiophene) and optical properties of
nondoped and doped polymers)

IT 7553-56-2, Iodine, uses

(dopant; prepn. of a sol. and neutral hexyl deriv. of
poly (3, 4-ethylene-dioxythiophene) and optical properties of
nondoped and doped polymers)

IT 350827-42-8P

(monomer; prepn. of a sol. and neutral hexyl deriv. of
poly (3, 4-ethylene-dioxythiophene) and optical properties of
nondoped and doped polymers)

IT 1295-35-8, Bis (1, 5-cyclooctadiene) nickel

(polymn. catalyst; prepn. of a sol. and neutral hexyl deriv. of
poly (3, 4-ethylene-dioxythiophene) and optical properties of
nondoped and doped polymers)

IT 350827-4 3-9P 351317-30-lP

(prepn. of a sol. and neutral hexyl deriv. of
poly (3, 4-ethylene-dioxythiophene) and optical properties of
nondoped and doped polymers)

IT 128-09-6, N-Chlorosuccinimide

(reactant in monomer prepn.; prepn. of a sol. and neutral hexyl
deriv. of poly (3, 4-ethylene-dioxythiophene) and optical
properties of nondoped and doped polymers)

L27 ANSWER 15 OF 26 HCA COPYRIGHT 2005 ACS on STN

135:107664 Fully undoped and soluble oligo (3, 4-ethylenedioxythiophene) s :

Truong 10/728,088

Page 43

spectroscopic study and electrochemical characterization. Tran-Van,
Francois; Garreau, Sebastien; Louarn, Guy; Froyer, Gerard; Chevrot,
Claude (Equipe Reactivite aux Interfaces (EA 2528) , Laboratoire sur
les Polymeres et les Materiaux Electroactif s, Universite de Cergy
Pontoise, Cergy Pontoise, 95013, Fr.). Journal of Materials
Chemistry, 11(5), 1378-1382 (English) 2001. CODEN: JMACEP. ISSN:
0959-9428. Publisher: Royal Society of Chemistry.

AB Fully undoped oligo (3, 4-ethylenedioxythiophene) s were synthesized
via polycondensation of the dibromo monomer in the presence of
NiBr2 (bpy) catalyst in N, N- dimethylacet amide (DMA). HPLC anal.
iridTcatea irharr^the material is constituted of" three main oligomers
which were clearly detected by UV-Visible spectroscopy. The
polythiophenes are partially sol. in DMA making them easier to
process to produce thin films of oligomers by evapn. of the solvent.
Electrochem. and electrochromic properties of undoped films were
studied. Deep purple in its undoped state, the material becomes sky
blue in the oxidized form. The mixt. of oligomers was characterized
by Raman scattering, IR absorption and X-Ray diffraction, and
compared to poly ( 3, 4-ethylenedioxy thiophene) obtained by the
oxidative route.

IT 174508-31-7P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene

(monomer; prepn. and redox electrochem. of electroactive fully
undoped and sol. oligo (3, 4-ethylenedioxythiophene) s)

RN 174508-31-7 HCA

CN Thieno[3, 4-b]-l, 4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

IT Polymers, preparation

(conjugated; prepn. and redox electrochem. of electroactive fully
undoped and sol. oligo (3, 4-ethylenedioxythiophene) s)

IT Polymerization

(dehalogenation condensation; prepn. and redox electrochem. of
electroactive fully undoped and sol. oligo (3,4-
ethylenedioxy thiophene) s)

IT Redox reaction

(electrochem.; prepn. and redox electrochem. of electroactive
fully undoped and sol. oligo (3, 4-ethylenedioxythiophene) s)

IT Polymer chains

(length, conjugation, low homogeneity; prepn. and redox

Truong 10/728,088 Page 44

electrochem. of electroactive fully undoped and sol.
oligo (3, 4-ethylenedioxythiophene) s)
IT Polymers, preparation

(polythiophenes, ethylenedioxythiophene, oligomeric; prepn. and
redox electrochem. of electroactive fully undoped and sol.
oligo (3, 4-ethylenedioxythiophene) s)
IT Conducting polymers

(polythiophenes; prepn. and redox electrochem. of electroactive
fully undoped and sol. oligo (3, 4-ethylenedioxythiophene) s)
IT Conjugation (bond)

Electrochromic materials
Electrochromism
Raman spectra
Redox potential

(prepn, and redox electrochem. of electroactive fully undoped and
sol . oligo (3, 4-ethylenedioxythiophene) s)
IT Band gap

(semiconductor; prepn. and redox electrochem. of electroactive

fully undoped and sol. oligo (3, 4-ethylenedioxythiophene) s)
IT 182628-58-6, (2,2' -Bipyridine) dibromonickel

(condensation polymn. catalyst; prepn. and redox electrochem. of

electroactive fully undoped and sol. oligo (3,4-

ethylenedioxythiophene) s)
IT 174508-31-7P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene

(monomer; prepn. and redox electrochem. of electroactive fully

undoped and sol. oligo (3, 4-ethylenedioxythiophene) s)
IT 163359-60-2P 350037-71-7P

(oligomeric; prepn. and redox electrochem. of electroactive fully

undoped and sol. oligo (3, 4-ethylenedioxythiophene) s)
IT 128-08-5, N-Bromosuccinimide 126213-50-1, 3,4-
Ethylenedioxythiophene

(prepn. and redox electrochem. of electroactive fully undoped and

sol . oligo (3, 4-ethylenedioxythiophene) s)
IT 127-19-5, N,N-Dimethylacetamide

(solvent; prepn. and redox electrochem. of electroactive fully

undoped and sol. oligo (3, 4-ethylenedioxythiophene) s)

L27 ANSWER 16 OF 26 HCA CORYRIGHT 2005 ACS on STN

134:287964 Organic compound fox organic electroluminescence member.

Hosokawa, Chishio; Ikeda, Shuji (Idemitsu Kosan Co., Ltd., Japan).
Jpn. Kokai Tokkyo Koho JP 20.01097949 A2 20010410, 28 pp.
(Japanese). CODEN: JKXXAF. \APPLICATION: JP 1999-277956 19990930.
AB The title org. compd. is repr^ented by

[Ar4Ar5C=CRl]s{ (Ar2)m(Arl)k(Ar^)n}w[R2C=CAr6Ar7] t (Arl = divalent
org. group; Ar2,3 = C6-30 aryle^e, etc.; Ar4-7 = C6-20 aryl, etc.;
Rl,2 = H, Cl-6 alkyl, etc.; m, n\ s, and t = 0, 1, 2). When the
org. compd. is used as a recombirvation site-forming substance and a
light-emitting material, the elecuroluminescence member gives* high

Truong 10/728, 088

Page 4 5

efficiency and long lifetime.
IT 174508-31-7

(org. compd. for org. electroluminescence member)
RN 174508-31-7 HCA

CN Thieno[3, 4-b]-l, 4-dioxin, 5, 7-dibromo-2, 3-dihydro- {9CI) (CA INDEX
NAME)

IT Electroluminescent devices

(org. compd. for)
IT 333432-12-5P 333432-1 4-7P 333432-1 6-9P 3334 32-18-lP
333432-20-5P 333432-22-7P 333432-24-9P

(org. compd. for org. electroluminescence member)
IT 15155-41-6 174508-31-7 201802-67-7 288105-04-4
333432-27-2 333432-28-3 333432-31-8

(org. compd. for org. electroluminescence member)

L27 ANSWER 17 OF 2 6 HCA COPYRIGHT 2005 ACS on STN
134:17569 Charge Transfer and Delocalization in Conjugated

(Ferrocenylethynyl) oligothiophene Complexes. Zhu, Yongbao; Wolf,
Michael 0. (Department of Chemistry, University of British Columbia,
Vancouver, BC, V6T IZl, Can.). Journal of the American Chemical
Society, 122(41), 10121-10125 (English) 2000. CODEN: JACSAT. ISSN:
0002-7863. OTHER SOURCES: CASREACT 134:17569. Publisher: American
Chemical Society.
AB Conjugated mono (ferrocenylethynyl) oligothiophene and

bis (ferrocenylethynyl) oligothiophene complexes were prepd. The
cyclic voltammograms of the complexes all contain a reversible
ferrocene oxidn. wave and an irreversible oligothiophene-based wave.
The p.d. between the two waves (AE) varies from 0.38 to 1.12
V, depending on the length and substitution of the oligothiophene
group. Several of the mono (ferrocenylethynyl) oligothiophene
complexes couple when oxidized, resulting in the deposition of a
redox-active film on the electrode surface. In soln., electrochem.
oxidn. of the Fell centers yields the corresponding monocations and
dications, which exhibit oligothiophene-to-Felll charge-transfer
transitions in the near-IR region. The band maxima of these
low-energy transitions correlate linearly with AE, while the
oscillator strengths show a linear correlation with neg. slope with
AE. The complexes with similar charge-transfer transition

Truong 10/728, 088

Page 4 6

dipole lengths show an increase in the extent of charge
delocalization with smaller AE. Comparisons between complexes
with different length oligothiophene ligands show that a redn. in
AE results either in greater delocalization of charge or in
charge being delocalized further along the rigid oligothiophene
ligand. These results have important implications in understanding
charge delocalization in metal-contg. polymers.

IT 174508-31~7P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene

(prepn., coupling with bromothiophene and conversion to monobromo
analog)

RN 174508-31-7 HCA

CN Thieno[3,4-b]-l,4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

IT Charge transfer transition

(LMCT; of conjugated mono (ferrocenylethynyl) oligothiophene and"

bis ( ferrocenylethynyl ) oligothiophene complexes )
IT Redox reaction

(electrochem. ; of mono ( f errocenylethynyl ) oligothiophene and

bis (ferrocenylethynyl) oligothiophene complexes)
IT Films

(electrochromic; formation on electrode surface of redox-active

films from mono (ferrocenylethynyl) oligothiophene complexes when

electrochem. oxidized)
IT Metallocenes

(ferrocenes; prepn., cyclic voltammetry, LMCT transitions and

delocalization in mono ( ferrocenylethynyl) oligothiophene and

bis (ferrocenylethynyl) oligothiophene complexes)
IT Electrochromic materials

(films; formation on electrode surface of redox-active films from

mono (ferrocenylethynyl) oligothiophene complexes when electrochem.

oxidized)
IT Electron delocalization

(in conjugated mono ( ferrocenylethynyl) oligothiophene and

bis (ferrocenylethynyl) oligothiophene complexes)
IT Linear free energy relationship

(of LMCT transitions and oscillator strengths of

mono (ferrocenylethynyl) oligothiophene and

bis (ferrocenylethynyl) oligothiophene complexes with p.d. between

Truong 10/728,088 Page 47

ferrocene oxidn. and oligothiophene-based waves)
IT Oxidation, electrochemical
Oxidation potential
Redox potential

(of mono (f errocenylethynyl) oligothiophene and
bis (f errocenylethynyl) oligothiophene complexes)
IT Oscillator strength

(of mono (f errocenylethynyl) oligothiophene and
bis (f errocenylethynyl) oligothiophene complexes in relation to
p.d. between ferrocene oxidn. and oligothiophene-based waves)
IT Coupling reaction

(of mono (f errocenylethynyl) oligothiophene complexes when
elect rochem. oxidized)
IT 126213-50-1, 3, 4-Ethylenedioxythiophene

(bromination of)
IT 1003-09-4, 2-Bromothiophene

(coupling reactions with dibromoethylenedioxythiophene and
ethynyl ferrocene)
IT 1271-47-2, Ethynylf errocene

(coupling reactions with halo-substituted thiophene oligomers)
IT 3141-27-3, 2, 5-Dibromothiophene 3480-11-3, 5-Bromo-2, 2 ' -

bithiophene 4805-22-5, 5, 5 ' -DiBromo-2, 2 ' -bithiophene 98057-08-0,
5,5' '-Dibromo-2,2' :5',2' ' -terthiophene 104499-98-1,
5-Iodo-2,2' :5',2' ' -terthiophene

(coupling with ethynylf errocene)
IT 309753-41-1 309753-42-2 309753-43-3 309753-44-4 309753-45-5
309753-4 6-6 309753-47-7 309753-4 8-8 309753-4 9-9 309753-50-2
(electrochem. formation, UV-visible-near-IR spectra and elec.
potential of couple contg.)
IT 309753-55-7P 309753-58-OP 309753-60-4P

(electrochromic films)
IT 309753-52-4P, 3 ' , 4 ' -Ethylenedioxy-2, 2 ' : 5 ' , 2 ' ' -terthiophene

(prepn. and bromination of)
IT 302554-82-lP, 2-Bromo-3, 4-ethylenedioxythiophene 309753-53-5P,

5-Bromo-3' , 4 ' -ethylenedioxy-2 , 2 ' :5' ,2' '-terthiophene 309753-54-6P,
5,5'' -Dibromo-3 ' , 4 ' -ethylenedioxy-2 , 2 ' : 5 ' , 2 ' ' -terthiophene
(prepn. and coupling with ethynylf errocene)
IT 174508-31-7P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene

(prepn., coupling with bromothiophene and conversion to monobromo
analog)

IT 1291-8 8-9P, 2-Ferrocenylethynyl thiophene 2 61 622-3 6-OP,
2, 5-Bis (f errocenylethynyl) thiophene 261622-40-6P,
5, 5 '-Bis (f errocenylethynyl) -2, 2' -bithiophene 2 61622-4 6-2P,
5,5'' -Bis (f errocenylethynyl) -2, 2 ' : 5' , 2 ' ' -terthiophene
309753-33-lP, 5-Ferrocenylethynyl-2, 2 ' -bithiophene 309753-35-3P,
5-Ferrocenylethynyl-2 , 2 ' : 5 ' , 2 ' ' -terthiophene 3097 53-3 6-4P,
5-Ferrocenylethynyl-3, 4-ethylenedioxythiophene 309753-37-5P,
5-Ferrocenylethynyl-3 ' , 4 ' -ethylenedioxy-2, 2 ' : 5 ' , 2 ' ' -terthiophene

Truong 10/728, 088

Page 4 8

309753-39-7P, 2, 5-Bis { f errocenylethynyl) -3, 4-ethylenedioxythiophene
309753-40-OP, 5,5'' -Bis (f errocenylethynyl) -3 ' , 4 ' -ethylenedioxy-
2, 2 ' : 5' , 2 ' ' -terthiophene

(prepn., cyclic voltamitietry, LMCT transitions and delocalization

in mono (f errocenylethynyl ) oligothiophene and

bis (f errocenylethynyl) oligothiophene complexes)

L27 ANSWER 18 -OF 2 6 HCA COPYRIGHT 2005 ACS on STN
133:223287 Synthesis and Electronic Structure Investigations of
a, o)-Bis (arylthio) oligothiophenes : Toward Understanding
Wire-Linker Interactions in Molecular-Scale Electronic Materials.
Hicks, Robin G.; Nodwell, Matthew B. (Department of Chemistry,
University of Victoria, Victoria, EC, V8W 3V6, Can.). Journal of
the American Chemical Society, 122(28), 6746-6753 (English) 2000.
CODEN: JACSAT. ISSN: 0002-7863. Publisher: American Chemical
Society.

AB Several oligothiophenes with 2-mesitylthio (MesS) substituents have
been prepd. and studied by UV-visible spectroscopy and cyclic
voltammetry. These compds. can be considered as models for
thiol-terminated conjugated oligomers, which have attracted intense
interest as materials for mol. -scale electronics. Three types of
oligomers were prepd.: a, ©-bis (mesitylthio) oligothiophen
es 4-7, a, ©-bis (mesitylthio) oligo (3, 4-
ethylelendioxythiophene) s 12-14, and a,co-

bis (mesitylthio) oligomers 15-19 contg. both thiophene and
3, 4-ethylenedioxythiophene rings. The mesitylthio groups were
introduced via nucleophilic attack of lithiated thiophenes on
mesitylenesulf enyl chloride. The oligomers were assembled by
oxidative coupling or palladium-catalyzed Stille coupling of
2-stannylthiophenes with 2-bromothiophenes . The soln. electronic
spectra of all oligomers display a red-shift in the lowest-energy
transition max. (A.max) relative to oligothiophenes lacking
the MesS- group. The red-shift arises from conjugative overlap of a
mesitylthio sulfur lone pair with the oligothiophene n system.
Cyclic voltammetry studies indicate that the MesS group
significantly lowers the first and second oxidn. potentials of the
oligomers and improves the stability of the incipient radical
cations and dications relative to alkyl-capped oligothiophenes.
Addnl., the difference between first and second oxidn. potentials in
the MesS-substituted oligomers is much lower than known
alkyl-substituted oligomers. This effect is due to the terminal
MesS groups which cause charge d. in the radical cations to cone, at
the chain ends, thereby lowering the Coulombic barrier to
introduction of a second charge. The electronic structure
perturbations caused by the MesS- group are discussed in the context
of single-mol. conduction in thiol-terminated conjugated oligomers
bound to gold electrodes.
IT 174508-31-7P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene

Truong 10/728; 088 Page 49

(synthesis and electronic structure of a,co-
bis (arylthio) oligothiophenes)
RN 174508-31-7 HCA

CN Thieno[3,4-b]-l, 4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

Br

IT Oxidation potential

(first, second; synthesis and electronic structure of
a, co-bis (arylthio) oligothiophenes)
IT Conducting polymers
Cyclic voltammetry

(synthesis and electronic structure of a,co-
bis (arylthio) oligothiophenes)
IT 291308-71-9P 291308-72-OP 291308-7 3- IP 291308-7 4-2P
291308-77-5P 2 91308-78- 6P 291308-7 9-7P 2 9130 8-8 0-OP
291308-81-lP 291308-82-2P 291308-83-3P 2 91308-85-5P
(synthesis and electronic structure of a,cD-
bis (arylthio) oligothiophenes)
IT 1541-10-2, Mesitylenethiol 3141-27-3, 2, 5-Dibromothiophene
(synthesis and electronic structure of a,co-
bis (arylthio) oligothiophenes)
IT 14575-12-3P, 2-Mesitylenesulf enyl chloride 174508-31-7P,

2, 5-Dibromo-3, 4-ethylenedioxythiophene 291308-70-8P 291308-75-3P
291308-76-4P

(synthesis and electronic structure of a,co-
bis (arylthio) oligothiophenes)

L27 ANSWER 19 OF 26 HCA COPYRIGHT 2005 ACS on STN

133:208463 Molecular Design and Characterization of Chromic Polyfluorene
Derivatives. Blondin, Pierre; Bouchard, Jimmy; Beaupre, Serge;
Belletete, Michel; Durocher, Gilles; Leclerc, Mario (Departement de
Chimie Centre de Recherche en Sciences et Ingenierie des
Macromolecules, Universite Laval, Quebec, QC, GIK 7P4, Can.).
Macromolecules, 33(16), 5874-5879 (English) 2000. CODEN: MAMOBX.
ISSN: 0024-9297. Publisher: American Chemical Society.

AB The thermochromic and solvatochromic properties of a series of

f luorene-based conjugated polymers have been investigated. Both
poly (2, 1- (9, 9-dioctylf luorene) ) and poly (2, 5- (thiophene) -alt-2, 7-
(9, 9-dioctylf luorene) ) have revealed interesting chromic properties

Truong 10/728,088 Page 50

which, on the basis of theor. calcns., seem to be related to a
relatively flexible backbone. On the other hand, the sterically
hindered, nonplanar poly (2, 5- (3, 4-dimethylthiophene ) -alt-2,7-(9,9-
dioctylf luorene) ) does not exhibit any significant solvatochromic
and thermochromic properties which could be explained by an
important energy barrier against planarity. Finally, investigations
on poly (2, 5- (3, 4-ethylenedioxythiophene) ~alt-2,7-(9,9-
dioctylf luorene) ) have revealed a highly conjugated conformational
structure which is not significantly modified upon temp, or solvent
changes .

IT 174508-31-7P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene

(mol. design and characterization of chromic polyf luorene
derivs . )
RN 174508-31-7 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2 , 3-dihydro- (9CI) (CA INDEX
NAME)

IT Polymers, properties

(f luorene-based; mol. design and characterization of chromic
polyf luorene derivs.)
IT Potential barrier
Potential energy
Solvatochromism
Thermochromi sm
UV and visible spectra

(mol. design and characterization of chromic polyf luorene
derivs . )
IT Bond angle

(torsional; mol. design and characterization of chromic
polyf luorene derivs.)
IT 123864-00-6, Poly (9, 9-dioctylf luorene) 222857-60-5 222857-62-
287924-57-6 2 87 924-58-7 287 92 4-59-8 2 87 924-60-1

(mol. design and characterization of chromic polyf luorene
derivs . )

IT 3141-26-2, 3, 4-Dibromothiophene

(mol. design and characterization of chromic polyf luorene
derivs . )

IT 74707-05-4P, 2 , 5-Dibromo-3, 4-dimethylthiophene 174508-31-7P
, 2, 5-Dibromo-3, 4-ethylenedioxythiophene

Truong 10/728,088 Page 51

(mol. design and characterization of chromic polyfluorene
derivs . )

L27 ANSWER 20 OF 26 HCA COPYRIGHT 2005 ACS on STN

133:164431 Light-Emitting Diodes from Fluorene-Based 7i-Conjugated

Polymers. Donat-Bouillud, Anne; Levesque, Isabelle; Tao, Ye;

D'lorio, Marie; Beaupre, Serge; Blondin, Pierre; Ranger, Maxime;

Bouchard, Jimmy; Leclerc, Mario (Institute for Microstructural

Sciences, National Research Council of Canada, Ottawa, ON, KIA 0R6,

Can.). Chemistry of Materials, 12(7), 1931-1936 (English) 2000.

CODEN: CMATEX. ISSN: 0897-4756. Publisher: American Chemical

Society.

AB The synthesis' of f luorene-based 7c-conjugated polymers was carried
out and the electroluminescent properties of the polymers were
studied. The photo- and electroluminescence of poly (dioctylf luorene-
phenylene)s and poly (dioctylf luorene-thiophene) s whose synthesis was
recently published was also studied. The alternate incorporation of
phenylene or thiophene moieties in f luorene-based 7c-conjugated
polymers was used to effect tunability of electroluminescent
properties. The spectral emission varies from blue to green or
yellow, depending on the compn. of the copolymers. To enhance the
luminescence efficiency of polymer assemblies, hole injection and
hole transport into the polymer were improved by insertion of an
insulating buffer layer and the incorporation of efficient hole
transport material in the polymer. The insertion of a charge
injection layer such as LiF and a hole transport layer such as
N,N'-diphenyl-N,N'' -bis (3-methylphenyl) -1, l-biphenyl-4 , 4 ' -diamine
significantly improved the electroluminescence efficiency of a test
diode from 4 . 5 to 125 cd/m2 .

IT 174508-31-7P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene

(monomer; prepn. of poly (dioctylf luorene-thiophene) s with tunable
electroluminescence and improved carrier transport for use in
light-emitting diodes)

RN 174508-31-7 HCA

CN Thieno[3,4-b]-l,4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

Br

IT Polymerization

(Suzuki coupling; prepn. of poly (dioctylf luorene-thiophene) s with

Truong 10/728, 088

Page 52

tunable electroluminescence and improved carrier transport for
use in light-emitting diodes)

IT Polymers, preparation

(conjugated; prepn. of poly (dioctylf luorene-thiophene) s with
tunable electroluminescence and improved carrier transport for
use in light-emitting diodes)

IT Electroluminescent devices

(light emitting diodes; prepn. of poly (dioctylf luorene-
thiophene) s with tunable electroluminescence and improved carrier
transport for use in light-emitting diodes)

IT Polymers, preparation

(polythiophenes, polyf luorene; prepn. of poly (dioctylf luorene-
thiophene) s with tunable electroluminescence and improved carrier
transport for use in light-emitting diodes)

IT Conducting polymers
Elect rochromism
Hole transport

Luminescence, electroluminescence

Oxidation potential

Reduction potential

Suzuki coupling reaction

(prepn. of poly (dioctylf luorene-thiophene) s with tunable
electroluminescence and improved carrier transport for use in
light-emitting diodes)
IT Electric current carriers

(transport; prepn. of poly (dioctylf luorene-thiophene) s with
tunable electroluminescence and improved carrier transport for
use in light-emitting diodes)
IT 7789-24-4, Lithium fluoride (LiF) , properties

(carrier injection layer; prepn. of poly (dioctylf luorene-
thiophene) s with tunable electroluminescence and improved carrier
transport for use in light-emitting diodes)
IT 65181-78-4, N, N' -Diphenyl-N, N ' -bis (S-methylphenyl) -1, l-biphenyl-4 , 4

diamine

(hole transport layer; prepn. of poly (dioctylf luorene-thiophene) s
with tunable electroluminescence and improved carrier transport
for use in light-emitting diodes)

IT 195 602- 17- 6P, 2,2* -Bis (3, 4-ethylenedioxy) bithiophene

(monomer and intermediate; prepn. of poly (dioctylf luorene-
thiophene )s with tunable electroluminescence and improved carrier
transport for use in light-emitting diodes)

IT 74707-05-4P, 2, 5-Dibromo-3, 4-dimethylthiophene 174508-31-7P
, 2, 5-Dibromo-3, 4-ethylenedioxythiophene 287924-56-5P

(monomer; prepn. of poly (dioctylf luorene-thiophene) s with tunable
electroluminescence and improved carrier transport for use in
light-emitting diodes)

IT 7440-05-3, Palladium, uses

(polymn. catalyst; prepn. of poly (dioctylf luorene-thiophene) s

Truong 10/728,088 Page 53

with tunable electroluminescence and improved carrier transport

for use in light-emitting diodes)
IT 1 98964- 57-7P 198 964-62-4P 2 10347- 56- IP 2228 57- 60- 5P
222857- 62-7P 222857-64-9P 222857- 68-3P 222857- 69-4P
287924-57-6P 287924-58-7P 2 87924-59-8P 287 924- 60- IP
287924- 61-2P 287 924-62-3P

(prepn. of poly (dioctylf luorene-thiophene) s with tunable

electroluminescence and improved carrier transport for use in

light-emitting diodes)
IT 75-16-1, Methylmagnesium bromide 128-08-5, NBS 3141-26-2,
3, 4-Dibromothiophene 126213-50-1, 3, 4-Ethylenedioxythiophene

(prepn. of poly (dioctylf luorene-thiophene) s with tunable

electroluminescence and improved carrier transport for use in

light-emitting diodes)

L27 ANSWER 21 OF 26 HCA COPYRIGHT 2005 ACS on STN

131:138509 Molecular recognition properties of crown

ether-functionalized oligothiophenes . Rimmel, G.; Bauerle, P.
(Abteilung Organische Chemie II, Universitat Ulm, Ulm, 89081,
Germany), Synthetic Metals, 102(1-3), 1323-1324 (English) 1999.
CODEN: SYMEDZ. ISSN: 0379-6779. Publisher: Elsevier Science S.A..

AB The palladium-catalyzed cross-coupling of dibrominated thieno-crown
ethers and stannylated cyclohexyl-capped mono- or bithiophenes leads
to novel end-capped oligothiophenes f unctionalized with crown ether
units of different ring size which are directly linked to the
oligomeric 7i-system. The electrochem. properties of these
oligomers were studied in the presence of metal cations. Their
redox chem, is strongly influenced by the mol. recognition process
and by the polarity of the solvent system. Due to electrostatic
interactions between the complexed cation and the redox center, the
oxidn. of the oligothiophene 7i-system becomes more difficult
leading to an anodic shift of the oxidn. potential.

IT 163657-74-7 233756-39-3 233756-41-7

(prepn. and mol. recognition properties of crown
ether-functionalized oligothiophenes)

RN 163657-74-7 HCA

CN Thieno [3,4-b]-l,4,7,10, 13-pentaoxacyclopentadecin,

14, 16-dibromo-2, 3, 5, 6, 8, 9, 11, 12-octahydro- (9CI) (CA INDEX NAME)

Truong 10/728,088

Page 54

RN 233756-39-3 HCA

CN Thieno [3, 4-b] -1,4,7, 10, 13, 16-hexaoxacyclooctadecin,

17, 19-dibromo-2, 3, 5, 6, 8, 9, 11, 12, 14, 15-decahydro- (9CI) (CA INDEX
NAME)

RN 233756-41-7 HCA

CN Thiophene, 2, 5-dibromo-3, 4-bis [2- (2-methoxyethoxy) ethoxy] - (9CI)
(CA INDEX NAME)

MeO~ CH2 - CH2 - 0" CH2 ~ CH2 0

0- CH2- CH2- 0- CH2- CH2- OMe

IT Alkali metals, analysis

(ions; prepn. and mol. recognition properties of crown

ether- functionali zed oligothiophenes)
IT Molecular recognition

(prepn • and mol. recognition properties of crown

ether- functionali zed oligothiophenes)
IT Crown ethers

(prepn. and mol, recognition properties of crown

ether- functionali zed oligothiophenes)
IT 7439-93-2, Lithium, analysis 7440-09-7, Potassium, analysis
7440-23-5, Sodium, analysis 7440-39-3, Barium, analysis
14798-03-9, Ammonium, analysis

(prepn. and mol. recognition properties of crown

ether- functionali zed oligothiophenes)
IT 233756-27-9P 233756-29-lP 233756-30-4P 233756-32-6P
233756-34-8P 233756-36-OP

(prepn. and mol. recognition properties of crown

ether- functionali zed oligothiophenes)
IT 163657-74-7 218606-46-3 233756-37-1 233756-39-3
233756-41-7

(prepn. and mol, recognition properties of crown
ether- functionali zed oligothiophenes)

Truong 10/728,088

Page 55

L27 ANSWER 22 OF 26 HCA COPYRIGHT 2005 ACS on STN

131:74044 Synthesis of non-doped poly (3, 4-ethylenedioxythiophene) and

its spectroscopic data. Yamamoto, Takakazu; Abla, Mahmut (Research
Laboratory of Resources Utilization, Tokyo Institute of Technology,
Yokohama, Japan). Synthetic Metals, 100(2), 237-239 (English) 1999.
CODEN: SYMEDZ. ISSN: 0379-6779. Publisher: Elsevier Science S.A..

AB Non-doped poly ( 3, 4-ethylenedioxythiophene) (PEDOTh) has been
synthesized by Ni-promoted dehalogenation polymn, of the
corresponding 2,5-dichloro monomer. Its IR, NMR, and XRD data are
compared with those of PEDOTh prepd. by chem. oxidn. polymn.

IT 225518-49-OP, 2, 5-Dichloro-3, 4-ethylenedioxythiophene

(prepn. and polycondensation of dichloroethylenedioxythiophene
monomer)

RN 225518-49-0 HCA

CN Thieno[3, 4-b]-l, 4-dioxin, 5, 7-dichloro-2, 3-dihydro- (9CI) (CA INDEX
NAME)

CI

IT Polymerization catalysts

(nickel complex; for polycondensation of

dichloroethylenedioxythiophene monomer)
IT 1295-35-8, Bis ( 1 , 5-cyclooctadiene) nickel

(catalyst for polycondensation of dichloroethylenedioxythiophene)
IT 126213-50-1, 3, 4-Ethylenedioxythiophene

(chlorination; prepn. of dichloroethylenedioxythiophene monomer)
IT 111-78-4, 1, 5-Cyclooctadiene 366-18-7, 2,2 ' -Bipyridyl

(in catalyst for polycondensation of

dichloroethylenedioxythiophene)
IT 225518-49-OP, 2 , 5-Dichloro-3, 4-ethylenedioxythiophene

(prepn. and polycondensation of dichloroethylenedioxythiophene

monomer)

IT 225518-50-3P, 2, 5-Dichloro-3, 4-ethylenedioxythiophene homopolymer
(prepn. of undoped polymer by polycondensation)

IT 1 63359- 60-2P, Poly (3, 4-ethylenedioxythiophene-2 , 5-diyl)

(prepn. of undoped polymer by polycondensation of dichloro
monomer)

L27 ANSWER 23 OF 2 6 HCA COPYRIGHT 2005 ACS on STN
124:203512 Absorption Properties of Alkoxy-Substituted

Thienylene-Vinylene Oligomers as a Function of the Doping Level.

Truong 10/728,088

Page 56

Havinga, E.; Mutsaers, C. M. J.; Jenneskens, L. W. (Philips
Research Laboratories, Eindhoven, '5656 AA, Neth.). Chemistry of
Materials, 8(3), 769-76 (English) 1996. CODEN: CMATEX. ISSN:
0897-4756. Publisher: American Chemical Society.

AB In an attempt to improve on the properties of PEDOT

(poly (3, 4-ethylenedioxythiophene) ) as a stable, conducting, and
transparent coating we synthesized four different alkoxy-substituted
poly (thienylene-vinylene) s, 1-4, using the Stille coupling reaction.
The oligomers and polymers obtained were characterized and their
NIR-vis absorption spectra were measured as a function of doping,
both electrochem. as films and chem. in soln. Similar spectra of
PEDOT films were gathered for comparison. In PEDOT a change in
doping level does not change the energies of the absorption bands,
while for the other polymers the bands shift markedly and the NJR
peak at high doping level lies at a higher energy. The polymers 1-4
are much less suited for the intended coatings than PEDOT. Possible
reasons for this are discussed.

IT 173291-48-OP, 2, 5-Dibromo-3, 4-bis (dodecyloxy) thiophene
173291-49-lP, 2, 5-Dibromo-3, 4-dibutoxythiophene
173291-50-4P

(monomer; absorption properties of alkoxy-substituted
thienylene-vinylene oligomers as a function of the doping level)
RN 173291-48-0 HCA

CN Thiophene, 2, 5-dibromo-3, 4-bis (dodecyloxy) - (9CI) (CA INDEX NAME)

Me- (CH2) 11-0 0- (CH2) ii-Me

RN 173291-49-1 HCA

CN Thiophene, 2, 5-dibromo-3, 4-dibutoxy- (9CI) (CA INDEX NAME)

n-BuO OBu-n

RN 173291-50-4 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2-hexyl-2, 3-dihydro- (9CI)
(CA INDEK NAME)

Truong 10/728,088

Page 57

Me- (CH2)5

IT Electric conductivity and conduction
Electric conductors, polymeric
Oscillator strength
Ultraviolet and visible spectra

(absorption properties of alkoxy-substituted thienylene-vinylene
oligomers as a function of the doping level)
IT Infrared spectra

(near-; absorption properties of alkoxy-substituted
thienylene-vinylene oligomers as a function of the doping level)
IT Coating materials

(elec. conductive, transparent, absorption properties of
alkoxy-substituted thienylene-vinylene oligomers as a function of
the doping level)

IT Energy level, band structure

(gap, absorption properties of alkoxy-substituted
thienylene-vinylene oligomers as a function of the doping level)

IT Electric potential

(oxidn,, absorption properties of alkoxy-substituted
thienylene-vinylene oligomers as a function of the doping level)

IT Polymers, properties

(polythiophenes, -vinylenes; absorption properties of
alkoxy-substituted thienylene-vinylene oligomers as a function of
the doping level)

IT 126213-54-5P 173291-56-OP 174592-79- IP

(absorption properties of alkoxy-substituted thienylene-vinylene

oligomers as a function of the doping level)
IT 126213-51-2, Poly (3, 4-ethylenedioxythiophene)

(absorption properties of alkoxy-substituted thienylene-vinylene

oligomers as a function of the doping level)
IT 994-89-8P, Tributylethynyltin

(absorption properties of alkoxy-substituted thienylene-vinylene

oligomers as a function of the doping level)
IT 84t58-2, 2, 3-Dicyano-5, 6-dichloro-l , 4-benzoquinone 7705-08-0,
Ferric chloride, reactions

(dopant; absorption properties of alkoxy-substituted

thienylene-vinylene oligomers as a function of the doping level)
IT 128-08-5, N-Bromosuccinimide 120621-18-3, 3- (Dodecyloxy) thiophene

(monomer synthesis; absorption properties of alkoxy-substituted

Truong 10/728, 088

Page 58

thienylene-vinylene oligomers as a function of the doping level)
14275-61-7P, (E) -1, 2-Bis ( tributyltin) ethylene 173291-47-9P,
2, 5-Dibromo-3- (dodecyloxy) thiophene 173291-48-OP,
2, 5-Dibromo-3, 4-bis (dodecyloxy) thiophene 173291-49-lP,
2, 5-Dibromo-3, 4-dibutoxythiophene 173291-50-4P

(monomer; absorption properties of alkoxy-substituted
thienylene-vinylene oligomers as a function of the doping level)
173291-51-5P, (E) -1, 2-Bis (tributyltin) ethylene-2, 5-dibromo-3-
(dodecyloxy) thiophene copolymer 173291-52-6P 173291-53-7P
173291-54-8P 1732 91-55-9P 174592-8 0-4 P

(oligomeric; absorption properties of alkoxy-substituted
thienylene-vinylene oligomers as a function of the doping level)
14221-01-3, Tetrakis (triphenylphosphine) palladium (0)

(polymn. catalyst; absorption properties of alkoxy-substituted
thienylene-vinylene oligomers as a function of the doping level)
77214-82-5P

(polymn. catalyst; absorption properties of alkoxy-substituted
thienylene-vinylene oligomers as a function of the doping level)

ANSWER 24 OF 26 HCA COPYRIGHT 2005 ACS on STN
203135 Electrochromic Conducting Polymers via Electrochemical
Polymerization of Bis (2- (3, 4-ethylenedioxy) thienyl) Monomers.
Sotzing, Gregory A. ; Reynolds, John R.; Steel, Peter J, (Center for
Macromolecular Science and Engineering, University of Florida,
Gainesville, FL, 32611, USA). Chemistry of Materials, 8(4), 882-9
(English) 1996. CODEN: CMATEX. ISSN: 0897-4756. Publisher:
American Chemical Society.

A series of bis (2- (3, 4-ethylenedioxy) thiophene) -based monomers were

synthesized and fully characterized; specifically

(E) -1, 2-bis (2- (3, 4-ethylenedioxy) thienyl) vinylene (BEDOT-V) ,

1. 4- bis (2- (3, 4-ethylenedioxy) thienyl ) benzene (BEDOT-B) ,

4, 4 '-bis (2- (3, 4-ethylenedioxy) thienyl) biphenyl (BEDOT-BP) ,

2. 5- bis (2- (3, 4-ethylenedioxy) thienyl) furan, 2, 5-bis (2- (3, 4-
ethylenedioxy) thienyl ) -thiophene (BEDOT-T) , and 2, 2 ' : 5 ' , 2 ' ' -ter (3, 4-
ethylenedioxy) thiophene, TER-EDOT. The X-ray crystal structures of
BEDOT-V and BEDOT-B were detd. These monomers oxidize and
polymerize at low potentials relative to other reported
electropolymerizable heterocycles . The electroactive polymers
formed have low redox switching potentials and are quite stable in
the conducting state. TER-EDOT had the lowest peak oxidn. potential
of +0.2 V vs Ag/Ag+, making it the most easily oxidized
polymerizable thiophene monomer reported. The electronic band gaps
of these EDOT based polymers were 1.4-2.3 eV (measured as the onset
of the Tc-Ti* transition) offering a diverse range of colors

which may prove useful in electrochromic devices. For example,
poly (BEDOT-V) is deep purple and opaque in the reduced state and
transmissive sky blue in the oxidized state, poly (BEDOT-T) is deep
blue opaque in the reduced state and transmissive blue in the

Truong 10/728,088

Page 59

oxidized state, while poly (BEDOT-BP) is transmissive orange in the
reduced state and opaque purple in the oxidized state. A thin film
of poly (BEDOT-V) switched rapidly between redox states (under 2 s)
with an initial optical contrast of 43%. This polymer retained 47%
of its optical contrast and 48% of its original charge d. after 600
double potential steps.

IT 174508-31-7P

(intermediate; electrochromic conducting polymers via
electrochem. polymn. of bis (ethylenedioxy) thienyl) monomers)

RN 174508-31-7 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

Br

S

Br

IT Bond angle
Bond length
Crystal structure
Electric conductors, polymeric

(electrochromic conducting polymers via electrochem. polymn. of
bis (ethylenedioxy) thienyl) monomers)
IT Polymerization

(electrochem., electrochromic conducting polymers via
electrochem. polymn. of bis (ethylenedioxy) thienyl) monomers)
IT Energy level, band structure

(gap, electrochromic conducting polymers via electrochem. polymn.
of bis (ethylenedioxy) thienyl) monomers)
IT Polymers, preparation

(polythiophenes, electrochromic conducting polymers via
electrochem. polymn. of bis (ethylenedioxy) thienyl ) monomers)
IT Crystallography

(x-ray, electrochromic conducting polymers via electrochem.
polymn. of bis (ethylenedioxy) thienyl) monomers)
IT 162899-00-5P 168 641-4 7-2P 168641-4 8-3P 174508-35-lP
174508-3 6-2P 174 508-37-3P

(electrochromic conducting polymers via electrochem. polymn. of
bis (ethylenedioxy) thienyl) monomers)
IT 32460-00-7P, 2 , 5-Dibromof uran . 162898-99-9P 168641-43-8P
174508-31-7P

(intermediate; electrochromic conducting polymers via
electrochem. polymn. of bis (ethylenedioxy) thienyl) monomers)

Truong 10/728,088 Page 60

IT 16864 1-44-9P 174508-32-8P 174 508-33- 9P 174 508-34 -OP

(monomer; electrochromic conducting polymers via electrochem.
polymn. of bis (ethylenedioxy) thienyl) monomers)
IT 196-37-6, p-Dibromobenzene. 110-00-9, Furan 156-60-5
3141-27-3, 2, 5-Dibromothiophene 126213-50-1, 3, 4-
Ethylenedioxythiophene

(starting material; electrochromic conducting polymers via
electrochem. polymn. of bis (ethylenedioxy) thienyl) monomers)

L27 ANSWER 25 OF 2 6 HCA COPYRIGHT 2005 ACS on STN

122:315261 Synthesis and characterization of thiophenes, oligothiophenes
and polythiophenes with crown ether units in direct
7i-conjugation. Baeuerle, P.; Scheib, St. (Inst. Organische
Chemie, Universitaet Wuerzburg, Wuerzburg, D-97074, Germany) . Acta
Polymerica, 46(2), 124-9 (English) 1995. CODEN: ACPODY. ISSN:
0323-7648. Publisher: VCH.

AB I (R,R' = 2-thiophenyl; R,R' = H; R = H, R^ - 2-thiophenyl ) were
prepd. by substitution of I (R,R' = Br) with 2- •
(trimethylstannyl) thiophene, deacylation of I (R,R' =
ethyloxycarbonyl) , and substitution of I (R H, R' =
trimethylstannyl). I (R,R' = H; R = H, = 2-thiophenyl) were
polymd. potentiodynamically to prep, selectively conducting
polythiophenes with crown ether units in direct Ti-conjugation.
The redox behavior of polymer films was characterized by cyclic
voltammograms in MeCN solns. in the presence of Li+, Na+, and K+
cations, and by spectroelectrochem. measurements. The redox
behavior of I (R,R' = H) polymer was effected by the introduction of
cations, whereas that of I (R = H, R' = 2-thiophenyl) polymer was
not. The sensitivity of I (R,R' = H) polymer to cations increased
in the order: Na+ >> Li+ > K+.

IT 163657-74-7P

• r

Truong 10/728,088 Page 61

(prepn. and electrochem. properties of thiophenes and
polythiophenes with crown ether units in direct 7c-conjugatidn)
RN 163657-74-7 HCA

CN Thieno [3, 4-b] -1,4,7, 10, 13-pentaoxacyclopentadecin,

14, 16-dibromo-2, 3, 5, 6, 8, 9, 11, 12-octahydro- (9CI) (CA INDEX NAME)

IT Electric conductors, polymeric
Electric current

(prepn. and electrochem. properties of thiophenes and
polythiophenes with crown ether units in direct Tc-conjugation)

IT Polymerization

(electrochem., prepn. and electrochem. properties of thiophenes
and polythiophenes with crown ether units in direct
TT-conjugation)

IT Electric potential

(oxidn., prepn. and electrochem. properties of thiophenes and
polythiophenes with crown ether units in direct Ti-conjugation)

IT Polymers, preparation

(polythiophenes, crown ether group-contg. , prepn. and
electrochem. properties of thiophenes and polythiophenes with
crown ether units in direct Ti-conjugation)

IT 3109-63-5, Tetrabutylammonium hexaf luorophosphate 7601-89-0,

Sodium perchlorate 7791-03-9, Lithium perchlorate 17084-13-8,
Potassium hexaf luorophosphate

(prepn. and electrochem. properties of thiophenes and
polythiophenes with crown ether units in direct 7c-conjugation)

IT . 163657-76-9P 163657-77-OP

(prepn. and electrochem. properties of thiophenes and
polythiophenes with crown ether units in direct ^-conjugation)

IT 163657-78-lP 1 63657-7 9-2P

(prepn. and electrochem. properties of thiophenes and
polythiophenes with crown ether units in direct Tt-conjugation)

IT 1066-45-1, Trimethylstannyl chloride 3437-95-4, 2-Iodothiophene
37496-13-2, 2- (Trimethylstannyl) thiophene 122372-64-9
(prepn. and electrochem. properties- of thiophenes and
polythiophenes with crown ether units in direct 7t-conjugation)

IT 163657-75-8P

(prepn. and electrochem. properties of thiophenes and
polythiophenes with crown ether units in direct 7t-conjugation)

%

Truong 10/728,088

Page 62

IT 163657-74-7P

(prepn. and electrochem. properties of thiophenes and
polythiophenes with crown ether units in direct 7t-conjugation)

L27 ANSWER 2 6 OF 26 HCA COPYRIGHT 2005 ACS on STN

69:35839 Synthesis in the thiophene series. Morel, Jean; Pasteur, Paul
(Lab. Chim. Org., Fac. Sci. Rouen, Mont-St . -Aignan, Fr.). Bulletin
de la Societe Chimique de France (2), 737-8 (French) 1968. CODEN:
BSCFAS. ISSN: 0037-8968.

GI For diagram(s) , see printed OA Issue.

AB Treatment of I (R = C02H) with S0C12 gave I (R = COCl), m.

94°, which was treated with NH3 in ether soln. to give 74% I
(R = C0NH2) (II), m. 247°. II was treated with P0C13 to give
90% I (R = CN) , m. 132°, which was reduced with LiAlH4 to '
give 43% I (R = CHO) , m. 122°. A mixt. of 2.8 g. I (R =
C02H) and 16 g. Hg(0Ac)2 in 50 cc. HOAc was refluxed 15 min., mixed
with a slight excess of iodine, and extd. with ether to give 19% I
(R = I) (III), m. 74°. Ill treated with BuLi followed by
HC0NMe2 gave 37% I (R = CHO), and with MeC0NMe2 gave 35% I (R = Ac),
m. 182°.

IT 19848-31-8P

(prepn. of)

RN 198-48-31-8 HCA

CN Thiophene, 2, 5-diiodo-3, 4-dimethoxy- (8CI) (CA INDEX NAME)

MeO OMe

IT 19848-26-lP 19848-27-2P 19848-28-3P 19848-29-4P 19848-30-7P
19848-31-8P 19989-07-2P
(prepn. of)

=> d 128 1-4 ti

L28 ANSWER 1 OF 4 HCA COPYRIGHT 2005 ACS on STN
TI Characterization of Organic p/n Junction Photodiodes Based on
Poly (alkyl thiophene) /Perylene Diimide Bilayers

L28 ANSWER 2 OF 4 HCA ' COPYRIGHT 2005 ACS on STN
TI Optical and redox properties of a series of 3,4-
ethylenedioxythiophene oligomers

L28 ANSWER 3 OF 4 HCA COPYRIGHT 2005 ACS on STN

Truong 10/728,088 Page 63

TI Temperature-dependent electrical conductivity of p-doped

poly(3, 4-ethylenedioxythiophene) and poly (3-alkylthiophene) s

L28 ANSWER 4 OF 4 HCA COPYRIGHT 2005 ACS on STN
TI Methylenedioxyhetarenes. 2. Reactions of diethyl
3, 4-methylenedioxy-2, 5-thiophenedicarboxylate

=> d 128 1-4 cbib abs hitstr it

L28 ANSWER 1 OF 4 HCA COPYRIGHT 2005 ACS on STN

139:93393 Characterization of Organic p/n Junction Photodiodes Based on
Poly (alkylthiophene) /Perylene Diimide Bilayers. Tan, Li; Curtis, M.
David; Francis, A. H. (Macromolecular Science & Engineering Center
and Department of Chemistry, The University of Michigan, Ann Arbor,
MI, 48109-1055, USA). Chemistry of Materials, 15(11), 2272-2279
(English) 2003. CODEN: CMATEX. ISSN: 0897-4756. Publisher:
American Chemical Society.

AB Photoconduction of bilayer org. p/n junction photocells can be
finely tuned through the alteration of either the side chain
orientation (regiorandom vs. regioregular) or main chain structure
in poly (3-alkylthiophene) s (P3ATs) , where the incorporation of an
electron-donating group (EDOT) appears to be an excellent method for
enhancing the photoconduction. also, doping of P3ATs proved to be an
equally viable route for tuning the device characteristics. These
polymers were used to fabricate bilayer org. photocells with the
polymer as the p-type layer and 1, 2-diaminobenzeneperylene-3, 4, 9, 10-
tetracarboxylic acid diimide (PV) as the n-type layer. Action
spectra at steady-state illumination demonstrated that all the
interfaces (org, -org. p/n junction and org. -electrode) are actively
involved in the photogeneration of carriers. Crit. device
properties, for example, open-circuit voltage (Voc) and
short-circuit current (Isc), are not only dependent on the selection
of electrodes and org. materials but also greatly affected by the
illumination wavelength and intensity.

IT 174508-31-7P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene
(prepn. of)

RN 174508-31-7 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

Truong 10/728, 088

Page 64

Electric current carriers

(generation; properties of org. pn photodiodes based on

polyalkylthiophenes and diaminobenzeneperylenetetracarboxylic

acid diimide)
Glass substrates

(in fabrication of org. pn photodiodes based on

polyalkylthiophenes and diaminobenzeneperylenetetracarboxylic

acid diimide)
Cyclic voltammetry

(of polyalkylthiophene derivs.)
Band gap

(optical; of polyalkylthiophene derivs.)
Conducting polymers

(polythiophenes; properties of org. pn photodiodes based on

polyalkylthiophenes and diaminobenzeneperylenetetracarboxylic

acid diimide)
Absorption spectra
Dopants

Electric current-potential relationship
Electrodes

Open circuit potential

Optical absorption

Photoconductivity

Photocurrent

Photodiodes

Short circuits

Solid-solid interface

(properties of org. pn photodiodes based on polyalkylthiophenes
and diaminobenzeneperylenetetracarboxylic acid diimide)

Coating process

(spin; in fabrication of org. pn photodiodes based on
polyalkylthiophenes and diaminobenzeneperylenetetracarboxylic
acid diimide)

104-15-4, Toluenesulfonic acid, uses 7647-01-0, Hydrogen chloride,
uses 7664-93-9, Sulfuric acid, uses 14635-75-7, Nitrosonium
tetraf luoroborate

(P30T dopant; properties of org. pn photodiodes based on
polyalkylthiophenes and diaminobenzeneperylenetetracarboxylic

Truong 10/728,088 Page 65

acid diimide)
98837-51-5, Poly (3-butylthiophene)

(UV spectra of)
7440-22-4, Silver, uses

(contact; properties of org. pn photodiodes based on
polyalkylthiophenes and diaminobenzeneperylenetetracarboxylic
acid diimide)
116971-10-9, 2, 5-Dibroino-3-butylthiophene

(in prepn. of butylthiophene-ethylenedioxythiophene copolymer)
126213-50-1, 3, 4-Ethylenedioxythiophene

(in prepn. of dibromoethylenedioxythiophene)
554459-31-3P, 2, 5-Dibromo-3-butylthiophene-2, 5-dibromo-3, 4-
ethylenedioxythiophene copolymer

(prepn. and properties of)
174508-31-7P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene

(prepn. of)
50926-11-9, ITO 55034-79-2

(properties of org. pn photodiodes based on polyalkylthiophenes
and diaminobenzeneperylenetetracarboxylic acid diimide)
104934-51-2, Poly (3-octylthiophene)

(pure and doped; properties of org. pn photodiodes based on
polyalkylthiophenes and diaminobenzeneperylenetetracarboxylic
acid diimide)
7664-41-7, Ammonia, processes

(redn. of doped P30T with; properties of org. pn photodiodes
based on polyalkylthiophenes and diaminobenzeneperylenetetracarbo
xylic acid diimide)

L28 ANSWER 2 OF 4 HCA COPYRIGHT 2 0 05 ACS on STN

137:232315 Optical, and redox properties of a series of

3, 4-ethylenedioxythiophene oligomers. Apperloo, Joke J.;
Groenendaal, L. "Bert"; Verheyen, Hilde; Jayakannan, Manickam;
Janssen, Rene A. J.; Dkhissi, Ahmed; Beljonne, David; Lazzaroni,
Roberto; Bredas, Jean-Luc (Laboratory for Macromolecular and Organic
Chemistry, Eindhoven University of Technology, Eindhoven, 5600 MB,
Neth.). Chemistry--A European Journal, 8(10), 2384-2396 (English)
2002. CODEN: CEUJED. ISSN: 0947-6539. OTHER SOURCES: CASREACT
137:232315. Publisher: Wiley-VCH Verlag GmbH.

AB The optical and redox properties of a series of 3,4-

ethylenedioxythiophene oligomers (EDOTn, n = 1-4) and their
p, p' -unsubstituted analogs (Tn, n = 1-4) are described.
Both series are end capped with Ph groups to prevent irreversible
a-coupling reactions during oxidative doping. Absorption and
fluorescence spectra of both series reveal a significantly higher
degree of intrachain conformational order in the EDOTn oligomers.
Oxidn. potentials (EPAl and EPA2) detd. by cyclic voltammetry reveal
that those of EDOTn are significantly lower than the corresponding
Tn oligomers as a consequence of the electron-donating

Truong 10/728, 088

Page 66

3, 4-ethylenedioxy substitution. Linear fits of EPAl and EPA2 vs.
the reciprocal no. "of double bonds reveal significantly steeper
slopes for the EDOTn than for the Tn oligomers. This could indicate
a more effective conjugation for the EDOTn series, confirmed by the
fact that coalescence of EPAl and EPA2 is reached already at
relatively short chain lengths («5 EDOT units) in contrast
to the Tn series (> 10 thiophene units) . The stepwise chem. oxidn.
of the EDOTn and Tn oligomers in soln. was carried out to obtain
radical cations and dications. The energies of the optical
transitions of the radical cations and dications as detd. by
UV/Vis/NIR spectroscopy were similar for the two series. These
spectroscopic observations are consistent with quantum-chem. calcns.
performed on the singly charged mols. Cooling solns. contg.
T2*+, T3*+, ED0T2*+, and ED0T3*+ revealed the

reversible formation of dimers, albeit with a some-what different
tendency, expressed in the values for the dimerization enthalpy.
IT 174508-31-7P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene

(coupling; prepn. and optical and redox properties of a series of
3, 4-ethylenedioxythiophene oligomers)
RN 174508-31-7 HCA

CN Thieno[3,4-b]'l,4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

Br

IT Radical ions

(cations, formation, electronic and ESR spectra, and
dimerization; prepn. and optical and redox properties of a series
of 3, 4-ethylenedioxythiophene oligomers)

IT Exciton

(coupling in radical cation dimers; prepn. and optical and redox
properties of a series of 3, 4-ethylenedioxythiophene oligomers)
IT Cations

(divalent; prepn. and optical and redox properties of a series of

3, 4-ethylenedioxythiophene oligomers)
IT • Substituent effects

(ethylenedioxy; prepn. and optical and redox properties of a

series of 3, 4-ethylenedioxythiophene oligomers)
IT CI (molecular orbital method)
Oscillator strength

(in electronic excitation of radical cations; prepn. and optical

Truong 10/728, 088

Page 67

and redox properties of a series of 3, 4-ethylenedioxythiophene
oligomers)
IT Conformation

(intrachain conformational order; prepn. and optical and redox
properties of a series of 3, 4-ethylenedioxythiophene oligomers)
IT Dimerization

Dimerization enthalpy
. ESR (electron spin resonance)
Electronic excitation
Hyperfine coupling

(of radical cations; prepn. and optical and redox properties of a
series of 3, 4-ethylenedioxythiophene oligomers)
IT Chemical chains
Fluorescence
Homologous series
Oxidation potential
UV and visible spectra
Vibronic excitation

(prepn. and optical and redox properties of a series of
3, 4-ethylenedioxythiophene oligomers)
IT Oligomers

(prepn. and optical and redox properties of a series of
3, 4-ethylenedioxythiophene oligomers)
IT Conjugation (bond)

■ (7C-; prepn. and optical and redox properties of a series of
3, 4-ethylenedioxythiophene oligomers)
IT 29488-24-2, 2-Bromo-5-phenylthiophene

(boronation; prepn. and optical and redox properties of a series
of 3, 4-ethylenedioxythiophene oligomers)
IT 591-50-4, lodobenzene 625-88-7, 2, 5-Diiodothiophene 3339-80-8,
5, 5'-Diiodo-2, 2 '-bithiophene 24 388-23-6 104 4 99-99-2,
5,5' '-Diiodo-2,2' :5',2' ' -terthiophene 264282-36-2

(coupling; prepn. and optical and redox properties of a series of
3, 4-ethyrenedioxythiophene oligomers)
IT 174508-31-7P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene

4594 09-70-2P 4594 09-7 1-3P 459409-73-5P 4 594 09-74- 6P

(coupling; prepn. and optical and redox properties of a series of
3, 4-ethylenedioxythiophene oligomers)
IT 76-09-5, Pinacol

(cyclocondensation with boronic acid; prepn. and optical and
redox properties of a series of 3, 4-ethylenedioxythiophene
oligomers)
IT 2054 3 6-42-6 4594 09-82-6

(dimerization; prepn. and optical and redox properties of a
series of 3, 4-ethylenedioxythiophene oligomers)
IT 1665-32-3P, 5,5' ' -Diphenyl-2, 2 ' :5',2' ' -terthiophene 83495-30-lP,
5, 5'-Diphenyl-2, 2'-bithiophene 4594 09-75-7P 459409-7 6-8P
459409-77-9P

Truong 10/728,088

Page 68

(electro- and chem. oxidn.; prepn. and optical and redox
properties of a series of 3, 4-ethylenedioxythiophene oligomers)

IT 238397-97-2P, 5,5' ' ' -Diphenyl-2, 2 ' : 5 ' , 2 ' ' : 5 ' ' , 2 » ' ^ -quaterthiophene
(electro- and chem. oxidn.; prepn. and optical and redox
properties of a series of 3, 4-ethylenedioxythiophene oligomers)

IT 1445-78-9P, 2, 5-Diphenylthiophene 459409-78-OP

(electrooxidn. ; prepn. and optical and redox properties of a
series of 3, 4-ethylenedioxythiophene oligomers)

IT 185258-96-2 459409-83-7

(oxidn. and dimerization; prepn. and optical and redox properties
of a series of 3, 4-ethylenedioxythiophene oligomers)

IT 459409-85-9

(oxidn.; prepn. and optical and redox properties of a series of

3, 4-ethylenedioxythiophene oligomers)
IT 4594 09-79-lP 4 59409-8 0-4P

(prepn. and optical and redox properties of a series of

3, 4-ethylenedioxythiophene oligomers)
IT 459409-81-5 4 59409-84-8 459409-8 6-0 4594 09-87-1 4594 09-88-2

(prepn. and optical and redox properties of a series of

3, 4-ethylenedioxythiophene oligomers)
IT 98-80-6, Phenylboronic acid

(prepn. and optical and redox properties of a series of

3, 4-ethylenedioxythiophene oligomers)
IT 126213-50-1, 3, 4-Ethylenedioxythiophene

(reactions; prepn, and optical and redox properties of a series

of 3, 4-ethylenedioxythiophene oligomers)
IT 459409-72-4P

(reactions; prepn. and optical and redox properties of a series

of 3, 4-ethylenedioxythiophene oligomers)
IT 195602-17-6

(stannylation; prepn. and optical and redox properties of a

series of 3, 4-ethylenedioxythiophene oligomers)

L2'8 ANSWER 3 OF 4 HCA COPYRIGHT 2005 ACS on STN

131:5811 Temperature-dependent electrical conductivity of p-doped
poly (3, 4-ethylenedioxythiophene) and poly ( 3-alkylthiophene ) s .
Yamamoto, Takakazu; Abla, Mahmut; Shimizu, Takahisa; Komarudin,
Dahrma; Lee, Bang-Lin; Kurokawa, Eriko (Research Laboratory
Resources Utilization, Tokyo Institute Technology, Yokohama, 226,
Japan), Polymer Bulletin (Berlin), 42(3), 321-327 (English) 1999.
CODEN: POBUDR. ISSN: 0170-0839. Publisher: Springer-Verlag .

AB Temp . -dependent elec. cond. of the substituted polythiophenes

poly (3, 4-ethylenedioxythiophene) (PEDOTh) and head-to-tail type
poly (3-alkylthiophene) (HT-P3RTh) was measured. The elec. cond.
(a) of p-doped PEDOTh and HT-P3RTh obeys equations of a type,
In a = In aO - (T0/T)0.25, with the TO value of
^:«105-107 K.

IT 225518-49-OP

Truong 10/728, 088

Page 69

(monomer; temp. -dependent elec, cond. of p-doped substituted
polythiophenes)
RN 225518-49-0 HCA

CN Thieno[3,4-b]-l,4-dioxin, 5, 7-diGhloro-2, 3-dihydro- (9CI) (CA INDEX
NAME)

CI

IT Polymers, properties

(polythiophenes; temp . -dependent elec. cond. of p-doped
substituted polythiophenes)
IT Conducting polymers

Electric conductivity

(temp. -dependent elec. cond. of p-doped substituted
polythiophenes )

IT 7553-56-2, Iodine, uses 14946-92-0, Iron tetrachloride

(dopant; temp. -dependent elec. cond. of p-doped substituted
polythiophenes)

IT 110134-47-9, Poly(3-hexyl-2,5-thiophenediyl) 135899-67-1,

3-Thiophenepropanesulfonic acid homopolymer 216318-88-6,
Poly (3-methyl-2, 5-thiophenediyl)

(doped; temp. -dependent elec. cond, of p-doped substituted
polythiophenes)
IT 126213-50-lP

(in prepn. of dichloro thiophene monomer)
IT 163359-60-2P 225518-50-3P

(iodine- and iron tetrachloride-doped; temp . -dependent elec.
cond. of p-doped substituted polythiophenes)
IT 225518-49-OP

(monomer; temp . -dependent elec. cond. of p-doped substituted
polythiophenes )

L28 ANSWER 4 OF 4 HCA COPYRIGHT 2005^05 on STN

82:170765 Methylenedioxyhetarenes . 2. Reactions of diethyl

3, 4-methylenedioxy-2, 5-thiophenedicarboxylate • Dallacker, Franz;

Hues, Volker (Inst. Org. Chem., Tech. Hochsch. Aachen, Aachen, Fed..

Rep. Ger.). Chemische Berichte, 108(2), 576-81 (German) 1975.

CODEN: CHBEAM. ISSN: 0009-2940. OTHER SOURCES: CASREACT 82:170765.
GI For diagram(s), see printed CA Issue.

AB The sym. thiophene deriv. I (R = Ri = C02Et)' (II) was treated with

excess ale. KOH, N2H4.H20, and Br at pH 7 . 0 to give .apprx.100% I (R

Truong 10/728,088

Page 70

= Rl = C02H) (III)/ 79% I (R = Rl '= C0NHNH2) (IV), and extremely
light- and air-sensitive I (R = Rl = Br) (V), resp. Ill was
esterified to give I (R = Rl = C02Me) or chlorinated and aminated,
e.g. with NHS, to give I (R = Rl = C0NH2) (VI) . IV was condensed
with piperonal to yield the piperonylidene deriv. I (R = Rl =
CONHN:CHC6H302CH2-3, 4) and V converted into I (R = Rl = iodo) .
Boiling VI and P0C13 gave 54% I (R = Rl = CN) , which with H2S in
pyridine-EtSN gave 100% I (R = Rl = CSNH2) .

IT 55370-18-8P 55370-19-9P
(prepn. of)

RN 55370-18-8 HCA

CN Thieno[3,4-d]-l,3-dioxole, 4 , 6-dibronio- (9CI) (CA INDEX NAME)

Br

Br

RN 55370-19-9 HCA

CN Thieno[3,4-d]-l, 3-dioxole, 4,6-diiodo- (9CI) (CA INDEX NAME)

I

I

IT 55370-05-3

(bromination and hydrazinolysis and hydrolysis of)
IT 55370-20-2P

(prepn. and decarboxylation and esterif ication and reaction with

thionyl chloride)
IT 55370-12-2P 55370-24-6P

(prepn. and dehydration of)
IT 55370-26-8P 55370-28-OP

(prepn. and hydrolysis of)
IT 55370-11-lP

(prepn. and reaction with amines)
IT 55370-06-4P

(prepn. and reaction with bromine and methanol and thionyl

chloride)
IT 55370-08-6P

Truong 10/728,088

Page 71

(prepn. and reaction with piperonal)
IT 55370-30-4P

(prepn. and reaction with sodium sulfide)
IT 55370-07-5P 55370-09-7P 55370-10-OP 55370-13-3P 55370-14-4P
55370-15-5P 55370-16-6P 55370-17-7P 55370-18-8P
55370-19-9P 55370-21-3P 55370-22-4P 55370-23-5P
55370-25-7P 55370-27-9P 55370-29-lP 55370-31-5P
(prepn. of)
IT 120-57-0

(reaction of, with (methylenedioxy) thiophenecarbohydrazide)
IT 100-61-8

(reaction of, with (methylenedioxy) thiophenedicarboxylic acid)
IT 30525-89-4

(reaction of, with dibromobutanediol)
IT 14396-65-7

(reaction of, with formaldehyde)
IT 110-89-4, reactions

(with (methylenedioxy) thiophenedicarboxylic acid)

Truong 10/728,088

Page 1

=> d 126 1-29 cbib abs hitstr it

L2 6 ANSWER 1 OF 29 HCA COPYRIGHT 2005 ACS on STN

141:380500 Spray Coatable Electrochromic Dioxythiophene Polymers with
High Coloration Efficiencies. Reeves, Benjamin D.; Grenier,
Christophe R. G.; Argun, Avni A.; Cirpan, Ali; McCarley, Tracy D.;
Reynolds, John R. (Department of Chemistry, Center for
Macromolecular Science and Engineering, University of Florida,
Gainesville, FL, 32611-7200, USA). Macromolecules, 37(20),
7559-7569 (English) 2004. CODEN: MAMOBX. ISSN: 0024-9297.
Publisher: American Chemical Society.

AB Four new disubstituted propylenedioxythiophene polymers have been

synthesized by Grignard metathesis on the 1-5 g scale. All polymers
were found to be sol. in chloroform, methylene chloride, toluene,
and THF and were fully structurally characterized having GPC detd.
no.-av. mol. wts. ranging from 33000 to 47000 g mol-1. Dil. polymer
solns. in toluene exhibited strong red fluorescence with moderate
quantum efficiencies from 0.38 to 0.50. Homogeneous thin films were
formed by electropolymn. and spray casting polymer solns. onto^ ITO
coated glass slides at thicknesses of ca. 150 nm. The films were
electroactive, switching from a dark blue-purple to a transmissive
sky blue upon p-doping, often with subsecond switching times, and
high electrochromic contrast luminance changes (% AY) of
40-70%. These studies revealed that the branched derivs.,
[poly (3, 3-bis (2-ethylhexyl ) -3, 4-dihydro-2H-thieno [3, 4-
b] [1, 4]dioxepine) ] and [poly (6, 8-dibromo-3, 3-bis (2-
ethylhexyloxymethyl) -3, 4-dihydro-2H-thieno [ 3, 4-b] [ 1 , 4 ] dioxepine) ] ,
gave an electrochem. response and assocd. color change over a much
smaller voltage range in comparison to the linear chain substituted
derivs. , [poly (3, 3-dihexyl-3, 4-dihydro-2H-thieno [ 3, 4-

b] [1, 4] dioxepine) ] and [poly (3, 3-bis (octadecyloxymethyl) -3, 4-dihydro-
2H-thieno[3, 4-b] [1, 4]dioxepine) ] . Composite coloration efficiency
values were found up to 1365 cm2/C; this was considerably larger
than values obtained from previously studied alkylenedioxythiophene
based polymers (.apprx.375 cm2/C) .
IT 700817-04-5P 700817-06-7P 700817-08-9P
700817-10-3P

(monomer; prepn. and electrooptical properties of spray coatable
electrochromic dioxythiophene polymers)
RN 700817-04-5 HCA

CN 2H-Thieno[3, 4-b] [1, 4] dioxepin, 6, 8-dibromo-3, 3-dihexyl-3, 4-dihydro-
(9CI) (CA INDEX NAME)

Truong 10/728,088

Page 2

Br

Me- (CH2) 5
Me- (CH2)i

Br

RN 700817-06-7 HCA

CN 2H-Thieno [3, 4-b] [1, 4] dioxepin, 6, 8-dibromo-3, 3-bis (2-ethylhexyl) -3, 4-
dihydro- (9CI) (CA INDEX NAME) ■

Et Br

n-Bu- CH

Et

RN 700817-08-9 HCA

CN 2H-Thieno[3, 4-b] [1, 4]dioxepin, 6, 8-dibromo-3, 3-bis [ [ (2-

ethylhexyl) oxy ] methyl] -3, 4-dihydro- (9CI) (CA INDEX NAME)

Et Br

Br

n-Bu-CH- CH2-0

Et

RN 700817-10-3 HCA

CN 2H-Thieno [3, 4-b] [1, 4] dioxepin, 6, 8-dibromo-3, 4-dihydro-3, 3-
bis[ (octadecyloxy) methyl]- (9CI) (CA INDEX NAME)

Truong 10/728,088

Page 3

Me- (CH2) 17-O-CH2
Me- (CH2)l7-0-CH2

IT 700817-12-5P 700817-14-7P 700817-16-9P
700817-18-lP 783322-80-5P 783322-81-6P
783322-82-7P 783322-83-8P

(prepn. and electrooptical properties of spray coatable
electrochromic dioxythiophene polymers)
RN 700817-12-5 HCA

CN 2H-Thieno [3, 4-b] [1, 4] dioxepin, 6, 8-dibromo-3, 3-dihexyl-3, 4-dihydro-,
homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 700817-04-5 *
CMF C19 H30 Br2 02 S

Me-,(CH2) 5
Me- (CH2)

RN 700817-14-7 HCA

CN 2H-Thieno[3, 4-b] [1, 4 ] dioxepin, 6, 8-dibromo-3, 3-bis (2-ethylhexyl) -3, 4-
dihydro-, homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 700817-06-7

CMF C23 H38 Br 2 02 S

Truong 10/728,088

Page

Et Br

RN 700817-16-9 HCA

CN 2H-Thieno[3, 4-b] [1/ 4]dioxepin, 6, 8-dibromo-3 , 3-bis [ [ (2-

ethylhexyl)oxy]methyl]-3,4-dihydro-, homopolyitier (9CI) (CA INDEX
NAME)

CM 1 ■

CRN 700817-08-9

CMF C25 H42 Br2 04 S

RN 700817-18-1 HCA

CN 2H-Thieno [3, 4-b] [1, 4]dioxepin, 6, 8-dibromo-3, 4-dihydro-3, 3-

bis[ (octadecyloxy) methyl]-, homopolymer (9CI) (CA .INDEX NAME)

CM 1

CRN 700817-10-3

CMF C45 H82 Br2 04 S

Truong 10/728,088

Page

Br

Me- (CH2) 17-0-CH2
Me- (CH2)l7-0-CH2

Br

RN 783322-80-5 HCA

CN Poly [3, 4-dihydro-3, 3-bis t (octaciecyloxy)methyl] -2H-thieno [3, 4-
b] [l,4]dioxepin-6, 8-diyl] {9CI) (CA INDEX NAME)

Me- (CH2) 17-0-CH2
Me- (CH2) 17-0-CH2

J n

RN 783322-81-6 HCA

CN Poly [3, 3-bis [ [ (2-ethylhexyl) oxy] methyl] -3, 4-dihydro-2H-thieno [3, 4-
b] [1,4] dioxepin-6, 8-diyl] (9CI) (CA INDEX NAME)

n-Bu- CH- CH2- 0- CH2 0.

n

RN
CN

783322-82-7 HCA

Poly [3, 3-bis (2-ethylhexyl) -3, 4-dihydro-2H-thieno [3, 4-b] [1, 4]dioxepin
6, 8-diyl] (9CI) (CA INDEX NAME)

Truong 10/728, 088

Page

n

RN 783322-83-8 HCA

CN Poly (3, 3-dihexyl-3, 4-dihydro-2H-thieno [3, 4-b] [ 1, 4 ] dioxepin-6, 8-diyl)
(9CI) (CA INDEX NAME)

n

IT Polymerization

(Grignard; prepn. and electrooptical properties of spray coatable

electrochromic dioxythiophene polymers)
IT Polymerization

(electrochem. ; prepn. and electrooptical properties of spray

coatable electrochromic dioxythiophene polymers)
IT Band gap

(optical; prepn. and electrooptical properties of spray coatable
electrochromic dioxythiophene polymers)
IT Conducting polymers

(polythiophenes; prepn. and electrooptical properties of spray
coatable electrochromic dioxythiophene polymers)
IT Electrochromism

Luminescence, electroluminescence
Redox potential

(prepn. and electrooptical properties of spray coatable

Truong 10/728,088

Page 7

electrochromic dioxythiophene polymers)
IT Electrooptical effect

(switching; prepn. and electrooptical properties of spray
coatable electrochromic dioxythiophene polymers)
IT 104-76-7, 2-Ethyl-l-hexanol 105-53-3, Diethyl malonate 111-25-1,
Hexyl bromide 112-92-5, 1-Octadecanol 3296-90-0,
2, 2-Di (bromomethyl) -1, 3-diol 18908-66-2, 2-Ethylhexyl bromide
51792-34-8, 3, 4-Dimethoxythiophene

(monomer synthesis; prepn. and electrooptical properties of spray
coatable electrochromic dioxythiophene polymers)
IT 54662-33-8P 634591-75-6P 634591-77-8P 700816-90-6P
701209-98-5P

(monomer synthesis; prepn. and electrooptical properties of spray

coatable electrochromic dioxythiophene polymers)
IT 700816-98-4P 700817-00-lP 700817-04-5P
700817-06-7P 700817-08-9P 700817-10-3P

(monomer; prepn. and electrooptical properties of spray coatable

electrochromic dioxythiophene polymers)
IT 700817-12-5P 700817-14-7P 700817-16-9P
700817-18-lP 783322-80-5P 783322-81-6P
783322-82-7P 783322-83-8P

(prepn. and electrooptical properties of spray coatable

electrochromic dioxythiophene polymers)

L26 ANSWER 2 OF 29 HCA COPYRIGHT 2005 ACS on STN

141:314660 Synthesis and polymerization of perf luoroalkylated.

3, 4-propylenedioxythiophene. Dong, Jian-Hai; Meng, Wei-Dong; Qing,
Feng-Ling (Coll. Chem. Chem. Eng., Donghua Univ. , Shanghai, 200051,
Peop. Rep. China). ARKIVOC (Gainesville, FL, United States) (9),
9-14 (English) 2004. CODEN: AGFUAR. URL: http: //www.arkat-
usa.org/ark/journal/2004/Yuan/CY-1037L/CY-1037L.pdf Publisher:
Arkat USA Inc. .

AB A novel monomer, perf luoroalkylated 3, 4-propylenedioxythiophene, was
prepd. by trans-etherif ication reaction between 3,4-
dimethoxythiophene and perf luoroalkylated cycloalkylpropane-1, 3-
diol. Bromination of monomer followed by a Grignard metathesis
coupling reaction provided perf luoroalkylated poly (3,4-
propylenedioxythiophene) . This polymer was quite insol. in any
known solvent.
IT 768400-96-OP

(multi-step prepn. of perf luoroalkylated propylenedioxythiophene
monomer and its bromination followed by Grignard metathesis
coupling polymn.)
RN 768400-96-0 HCA

CN Spiro[cyclopentane-l, 3' (4 'H) - [2H] thieno [3, 4-b] [ 1 , 4 ] dioxepin] ,
6' , 8'-dibromo-3-methyl-4- (2, 2, 3, 3, 4, 4, 5, 5, 6, 6, 7, 7, 7-
tridecafluoroheptyl)-, homopolymer (9CI) (CA INDEX NAME)

Truong 10/728, 088

Page 8

CM 1

CRN 768400-95-9

CMF C19 HIS Br2 F13 02 S

Br

IT Polymerization

(Grignard, metathetic; multi-step prepn, of perf luoroalkylated
propylenedioxythiophene monomer and its bromination followed by
Grignard metathesis coupling polymn.)

IT Polymerization

(metathetic, Grignard; multi-step prepn. of perf luoroalkylated
propylenedioxythiophene monomer and its bromination followed by
Grignard metathesis coupling polymn.)

IT 3195-24-2P, Diethyl 2 , 2-diallylmalonate

(cyclization of; multi-step prepn, of perf luoroalkylated
propylenedioxythiophene monomer and its bromination followed by
Grignard metathesis coupling polymn.).

IT 768400-93-7P

(cycloaddn. of; multi-step prepn. of perf luoroalkylated
propylenedioxythiophene monomer and its bromination followed by
Grignard metathesis coupling polymn •)

IT 105-53-3, Diethyl malonate 106-95-6, Allyl bromide, reactions

355-43-1, Perfluorohexyl iodide 51792-34-8, 3 , 4-Dimethoxythiophene
(multi-step prepn. of perf luoroalkylated propylenedioxythiophene
monomer and its bromination followed by Grignard metathesis
coupling polymn.)

IT 768400-94-8P 7 68400-95-9P

(multi-step prepn. of perf luoroalkylated propylenedioxythiophene
monomer and its bromination followed by Grignard metathesis
coupling polymn.)

IT 768400-96-OP

(multi-step prepn. of perf luoroalkylated propylenedioxythiophene
monomer and its bromination followed by Grignard metathesis
coupling polymn.)

IT 169893-13-4P

(redn. of; multi-step prepn. of perf luoroalkylated
propylenedioxythiophene monomer and its bromination followed by
Grignard metathesis coupling polymn.)

Truong 10/728,088 ^ Page 9

L26 ANSWER 3 OF 29 HCA COPYRIGHT 2005 ACS on STN
141:89456 Copolymers of 3, 4-Ethylenedioxythiophene and of Pyridine
Alternated with Fluorene or Phenylene Units: Synthesis, Optical
Properties, and Devices. Aubert, Pierre-Henri; Knipper, Martin;
Groenendaal, Lambertus; Lutsen, Laurence; Manca, Jean; Vanderzande,
Dirk (IMOMEC Division, IMEC, Diepenbeek, B-3590, BelgJ.
Macromolecules, 37(11), 4087-4098 (English) 2004. CODEN: MAMOBX.
ISSN: 0024-9297. Publisher: American Chemical Society.
AB We report the synthesis of four conjugated copolymers based on

alkylated fluorene or phenylene units which band gap is tuned by the
regular insertion of an electron-donating or electron-withdrawing
unit, (3, 4-ethylenedioxy) thiophene and pyridine, resp. The (AB)n
regular sequence is achieved by Suzuki polycondensation reactions.
The characterization of the copolymers by size exclusion chromatog.
reveals chains lengths of about 20-30 repeat units (40-60 rings),
leading to a good processability for potential optical applications.
The 1:1 ratio between the two units improves the soly. of the
material in common org. solvents, allowing for physicochem.
characterizations. Raman and FT-IR expts. indicate that the
electronic structure of the backbone is rather benzenic in the
neutral (undoped) state, as opposed to a quinoic oxidized structure.
All copolymers exhibit interesting electrochromic properties as
attested by cyclic voltammetry and UV-vis expts. They reversibly
switch among the entire visible spectra, which is of particular
importance for display applications. Moreover, the EDOT-based
copolymers strongly absorb in the NIR window (1200 nm up to 3000 nm)
with some potential electrochromic applications related to this
spectral window. Light-emitting diodes were fabricated using these
copolymers as active layer. To improve hole, and electron injection,
the active layer was sandwiched between a

ITO/PEDOT:PSSA/copolymer/Ba/Al. The emitting properties were
studied on the base of photoluminescence (PL) and

electroluminescence (EL) expts. The spectral emission varies from
blue-green to yellow, depending on the compn. of the copolymers.
IT 174508-31-7P

(monomer; prepn. and optical properties of and LEDs from
copolymers prepd. from dibromoethylenedioxythiophene or
dibromopyridine and contg. fluorene or phenylene units)
RN 174508-31-7 HCA

CN Thieno[3,4-b]-l,4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

Truong 10/728,088

Page 10

Br

IT 126213-51-2, PEDOT

(prepn. and optical properties of and LEDs from copolymers prepd.

from dibromoethylenedioxythiophene or dibromopyridine and contg.

fluorene or phenylene units)
RN 126213-51-2 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 2, 3-dihydro-, homopolymer (9CI) (CA INDEX
NAME)

CM 1

CRN 126213-50-1
CMF C6 H6 02 S

IT 287924-59-8P 287924-60-lP 716377-30-9P
716377-31-OP 716377-32-lP

(prepn. and optical properties of and LEDs from copolymers prepd.

from dibromoethylenedioxythiophene or dibromopyridine and contg.

fluorene or phenylene units)
RN 287924-59-8 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2, 3-dihydro-, polymer with

2, 2'- (9, 9-dioctyl-9H-fluorene-2, 7-diyl)bis [4, 4, 5, 5-tetramethyl-l , 3, 2-
dioxaborolane] {9CI) (CA INDEX NAME)

CM 1

CRN 196207-58-6
CMF C41 H64 B2 04

Truong 10/728,088

Page 11

Me- (CH2) 7 (CH2) 7 -Me

CM 2

CRN 174508-31-7
CMF C6 H4 Br2 02 S

Br

Br

RN 287924-60-1 HCA

CN Poly [ (2, 3-dihydrothieno [3, 4-b] -1, 4-dioxin-5, 7-diyl) (9, 9-dioctyl-9H-
fluorene-2,7-diyl) ] (9CI) (CA INDEX NAME)

Me- (CH2) 7

(CH2) 7-Me

J n

RN 716377-30-9 HCA

CN 1, 3,2-Dioxaborolane, 2, 2 ' - [2, 5-bis (octyloxy) -1/ 4-

phenylene]bis [4, 4, 5, S-tetramethyl-, polymer with

5, 7-dibromo-2, 3-dihydrothieno [3, 4-b] -1, 4-dioxin (9Ci;

NAME)

(CA INDEX

Truong 10/728,088

CM 1

CRN 457931-26-9
CMF C34 H60 B2 06

Me- (CH2) 7" 0

Me 0-(CH2)7-Me

CM 2

CRN 174508-31-7
CMF C6 H4 Br2 02 S

Br

RN 716377-31-0 HCA

CN Poly[ (2,3-dihydrothieno[3,4-b]-l,4-dioxin-5,7-diyl) [2,5
bis(octyloxy)-l,4-phenylene] ] (9CI) (CA INDEX NAME)

Me- (CH2) 7-0

Me- (CH2) 7-0

Truong 10/728,088

Page

RN 716377-32-1 HCA

CN Boronic acid, [2, 5-bis (octyloxy) -1, 4-phenylene]bis-, polymer with
5,7-dibromo-2,3-dihydrothieno[3,4-b]-l,4-dioxin (9CI) (CA INDEX
NAME)

CM 1

CRN 406461-51-6
CMF C22 H40 B2 06

Me- (CH2) 7-0

0- (CH2) 7-Me

CM 2

CRN 174508-31-7
CMF C6 H4 Br 2 02 S

IT Polymers, preparation

(conjugated; prepn. and optical properties of and LEDs from
copolymers prepd. from dibromoethylenedioxythiophene or
dibromopyridine and contg. fluorene or phenylene units)

IT Doping

(electrochem. ; prepn. and optical properties of and LEDs from
copolymers prepd. from dibromoethylenedioxythiophene or
dibromopyridine and contg. fluorene or phenylene units)

IT Conduction electrons

(injection; prepn. and optical properties of and LEDs from
copolymers prepd. from dibromoethylenedioxythiophene or
dibromopyridine and contg. fluorene or phenylene units)

IT Band gap

Truong 10/728, 088

Page 14

(optical; prepn. and optical properties of and LEDs from
copolymers prepd. from dibromoethylenedioxythiophene or
dibromopyridine and contg. fluorene or phenylene units)
IT Band gap

Elect rochromism

Electroluminescent devices

Electronic structure

Glass substrates

Glass transition temperature

HOMO (molecular orbital)

IR spectra

LUMO (molecular orbital)
Luminescence

Luminescence, electroluminescence

Polymerization

Polymerization catalysts

Raman spectra

Redox potential

Redox reaction

Thermal stability

UV and visible spectra

(prepn. and optical properties of and LEDs from copolymers prepd.

from dibromoethylenedioxythiophene or dibromopyridine and contg.

fluorene or phenylene units)
IT 9003-53-6D, sulfonated

(PSS; prepn. and optical properties of and LEDs from copolymers

prepd. from dibromoethylenedioxythiophene or dibromopyridine and

contg. fluorene or phenylene units)
IT 7429-90-5, Aluminum, uses 7440-39-3, Barium, uses

(electrode; prepn. and optical properties of and LEDs from

copolymers prepd. from dibromoethylenedioxythiophene or

dibromopyridine and contg. fluorene or phenylene units)
IT 67399-94-4P, 1, 4-Dioctyloxybenzene 123863-99-OP,

9, 9-Dioctylf luorene 156028-40-9P, 1, 4-Dibromo-2, 5-
dioctyloxybenzene 198964-46-4P, 2 , 7-Dibromo-9, 9-dioctylf luorene

(intermediate in monomer prepn.; prepn. and optical properties of

and LEDs from copolymers prepd. from

dibromoethylenedioxythiophene or dibromopyridine and contg.
fluorene or phenylene units)

IT 174508-31-7P 196207-58-6P 4064 61-51-6P 457'931-26-9P

(monomer; prepn. and optical properties of and LEDs from
copolymers prepd. from dibromoethylenedioxythiophene or
dibromopyridine and contg. fluorene or phenylene units)

IT 14221-01-3, Pd(PPh3)4

(polymn. catalysts; prepn. and optical properties of and LEDs
from copolymers prepd. from dibromoethylenedioxythiophene or
dibromopyridine and contg. fluorene or phenylene units)

IT 50926-11-9, ITO 126213-51-2, PEDOT

Truong 10/728,088

Page 1

(prepn, and optical properties of and LEDs from copolymers prepd.

from dibromoethylenedioxythiophene or dibromopyridine and contg.

fluorene or phenylene units)
287924-59-8P 287924-60-lP 294637-16-4P
473914-21-5P 633290-76-3P 716377-30-9P
716377-31-OP 716377-32-lP 716377-33-2P
716377-34-3P

(prepn. and optical properties of and LEDs from copolymers prepd.
from dibromoethylenedioxythiophene or dibromopyridine and contg.
fluorene or phenylene units)
86-73-7, Fluorene 111-83-1, Octyl bromide 123-31-9,
Hydroquinone, reactions 61676-62-8, 2-Isopropoxy-4 , 4 , 5, 5-
tetramethyl- [1,3,2] dioxaborolane 126213-50-1

(reactant in monomer prepn.; prepn. and optical properties of and
LEDs from copolymers prepd. from dibromoethylenedioxythiophene or
dibromopyridine and contg. fluorene or phenylene units)

ANSWER 4 OF 29 HCA COPYRIGHT 2005 ACS on STN

39122 Synthetic methodology toward new propylenedioxythiophene
polymers. Reeves, Benjamin D.; Grenier, Christophe R. G.; Argun,
Avni A.; Cirpan, Ali; Cunningham, Garry B.; McCarley, Tracy D.;
Reynolds, John R. (Department of Chemistry, Center for
Macromolecular Science and Engineering, University of Florida,
Gainesville, FL, 32611, USA) . Polymer Preprints (American Chemical
Society, Division of Polymer Chemistry), 45(1), 284 (English) 2004.
CODEN: ACPPAY. ISSN: 0032-3934. Publisher: American Chemical
Society, Division of Polymer Chemistry.

An extensive family of dioxythiophene-based monomers by Williamson-
etherif ication, transetherif ication, and Mitsunobu chem. has been
successfully synthesized by our group, however, the routes developed
are not efficient when synthesizing monomers with large
substituents. Therefore, a new synthetic methodol. has been
employed to access monomers with large nonpolar derivs. First,
3, 4-dimethoxythiophene is subject to a transetherif ication reaction
with 2,2-bis(bromomethyl)-l,3-propanediol. The bromomethyl
derivatized ProDOT then undergoes a Williamson etherif ication with
octadecanol and the octadecyl deriv. was then brominated with NBS
followed by polymn. by Grignard metathesis. The resulting polymer
after purifn. by fractionation was characterized by NMR, GPC,
MALDI-TOF, X-ray powder diffraction, DSC, and TGA. The polymer was
highly sol. in org. solvents, which allowed the spray casting of
thin films from soln, and the films were then electrochromically
characterized and incorporated into dual polymer electrochromic
devices. Also, a polymer soln. in toluene gave a relatively high
fluorescence quantum efficiency with a value of 0.40.
700817-18-lP

(synthesis of propylenedioxythiophene polymers and fluorescence
thereof)

Truong 10/728, 088

Page 16

RN 700817-18-1 HCA

CN 2H-Thieno[3, 4-b] [1, 4] dioxepin, 6, 8-dibromo-3, 4-dihydro-3, 3-

bis[ (octadecyloxy)methyl]-, homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 700817-10-3

CMF C45 H82 Br2 04 S

Me- (CH2) 17-0-CH2 ^ 0,
Me- (CH2) 17-0-CH2.

IT Polymerization

(Grignard; synthesis of propylenedioxythiophene polymers and

fluorescence thereof)
IT Alkoxylation

(Williamson; synthesis of propylenedioxythiophene-based monomer

for polymers thereof)
IT Polymerization

(metathetic; synthesis of propylenedioxythiophene polymers and

fluorescence thereof)
IT Fluorescence

{of propylenedioxythiophene polymers)
IT Conducting polymers

(polythiophenes; synthesis of propylenedioxythiophene polymers

and fluorescence thereof)
IT Etherif ication

(transetherification; synthesis of propylenedioxythiophene-based

monomer for polymers thereof)
IT 3296-90-0 51792-34-8

(in synthesis of propylenedioxythiophene-based monomer for

polymers thereof)
IT 634591-77-8P 701209-98-5P

(in synthesis of propylenedioxythiophene-based monomer for

polymers thereof)
IT 700817-18-lP

(synthesis of propylenedioxythiophene polymers and fluorescence

thereof)
IT 700817-10-3P

(synthesis of propylenedioxythiophene-based monomer for polymers

thereof)

Truong 10/728, 088

Page 17

L26 ANSWER 5 OF 29 HCA COPYRIGHT 2005 ACS on STN

141:38937 Processable dioxythiophene based polymers with branched
substituents . Grenier, Christophe R. G.; Reeves, Benjamin D.;
Argun, Avni A.; Reynolds, John R. (Department of Chemistry, Center
for Macromolecular Science and Engineering, University of Florida,
Gainesville, FL, 32611, USA) . Polymer Preprints (American Chemical
Society, Division of Polymer. Chemistry) , 45(1), 262 (English) 2004.
CODEN: ACPPAY. ISSN: 0032-3934. Publisher: American Chemical
Society, Division of Polymer Chemistry.

AB We have developed a new family of branched dialkyl and dialkoxy
substituted poly (3, 4-propylenedioxythiophene) s (PProD0T-R2) .
Substituents are sym. placed at the 2 position of the propylene
bridge. For the monomer synthesis with R= (2-ethylhexyl) oxymethyl
and R= (2-methylbutyl) oxymethyl, we used the Williamson
etherification on ProDOT- (CH2Br) . For R=2-ethylhexyl, we applied
the transetherif ication technique on 3, 4-dimethoxythiophene with the
corresponding 2, 2-dialkylpropanediol, easily obtained via malonic
synthesis followed by redn. with LiAlH4 . The polymer synthesis was
carried out using Grignard Metathesis, yielding high mol. wt.
polymers (Mn=20, 000-50, 000 g.mol-1) and dispersities around 1.7.
These polymers possess excellent soly. in common org. solvents and
allow for easy processability . Spray coated thin films of
PProDOT- (CH20EtHx) and PProDOT- (EtHx) are electrochromic, switching
resp. from absorptive red-purple to a very transmissive light blue
color. They exhibit high coloration efficiencies (.apprx.2000
cm2/C) and extremely sharp spectroelectrochem. transitions within a
very narrow range of potential ( . apprx . 0 . IV) .

IT 700817-14-7P 700817-16-9P

(in prepn. of processable dioxythiophene based polymers with
branched substituents)

RN 700817-14-7 HCA

CN 2H-Thieno [3, 4-b] [ 1 , 4 ] dioxepin, 6, 8-dibromo-3, 3-bis (2-ethylhexyl ) -3, 4-
dihydro-, homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 700817-06-7

CMF C23 H38 Br2 02 S

Truong 10/728,088

Page

Et Br

RN 700817-16-9 HCA

CN 2H-Thieno [3, 4-b] [ 1, 4 ] dioxepin, . 6, 8-dibromo-3, 3-bis [ [ (2-

ethylhexyl) oxy]methyl] -3, 4-dihydro-, homopolymer (9CI) (CA INDEX
NAME)

CM 1

CRN 700817-08-9

CMF C25 H42 Br2 04 S

Et Br

Br

n-Bu-CH-CH2-0

Et

IT Alkylation
Bromination
Etherif ication
Reduction

(in prepn. of processable dioxythiophene based polymers with

branched substituents)
IT Polymerization

(metathetic; in prepn. of processable dioxythiophene based

polymers with branched substituents)
IT Solubility

{of processable dioxythiophene based polymers with branched

substituents)
IT Conducting polymers

Truong 10/728, 088

Page 19

(polythiophenes; prepn. of processable dioxythiophene based

polymers with branched substituents)
IT Electrochromic materials

(prepn. of processable dioxythiophene based polymers with

branched substituents)
IT Etherif ication

(transetherif ication; in prepn. of processable dioxythiophene •

based polymers with branched substituents)
IT 700817-14-7P 700817-16-9P

(in prepn. of processable dioxythiophene based polymers with

branched substituents)
IT 104-76-7, 2-Ethylhexanol 105-53-3, Diethyl malonate 18908-66-2,
l-Bromo-2-ethylhexane 51792-34-8, 3, 4-Dimethoxythiophene
701209-98-5

(in prepn. of processable dioxythiophene based polymers with
branched substituents)
IT 24251-94-3P 634 591-7 5- 6P 70081 6-90- 6P 7 008 17- 00- IP

(in prepn. of processable dioxythiophene based polymers with
branched substituents)

L26 ANSWER 6 OF 29 HCA COPYRIGHT 2005 ACS on STN

141:24056 Solution processable and electrochromic dioxythiophene-based
polymers. Reeves, Benjamin D.; Grenier, Christophe R. G.; Argun,
Avni A.; Cirpan, Ali; McCarley, Tracy D.; Reynolds, John R.
(Department of Chemistry, Center for Macromolecular Science and
Engineering, University of Florida, Gainesville, FL, 32611, USA) .
Polymer Preprints (American Chemical Society, Division of Polymer
Chemistry), 45(1), 180 (English) 2004. CODEN: ACPPAY. ISSN:
0032-3934. Publisher: American Chemical Society, Division of
Polymer Chemistry.

AB This work presents the development of a family of sol. processable
disubstituted propylenedioxythiophenes and an anal, of their
electrochromic properties. 2,5-Dibromo derivatized dioxythiophene
monomers underwent Grignard metathesis polymn. to afford org. sol.
neutral polymers. Polymers were characterized by NMR, GPC,
MALDI-TOF, X-ray powder diffraction, TGA, and DSC. Mol. wt.
characterization by GPC vs. polystyrene stds. indicated no. av. mol.
wts. between 7-40 kg/mol. MALDI-TOF studies were performed which
gave a set of dominant peaks sepd. by 322 amu, corresponding to the
mol. wt. of the monomer repeat unit. Thin films were- processed by
spray casting polymer solns. onto a working electrode.
Spectroelectrochem. , colorimetry, and composite coloration
efficiencies studies show that the spray cast polymers have the same
contrast ratio and switching speeds as the electrodeposited films of
the same thickness. The composite coloration efficiency values for
this family are two to three times larger than previously obsd. for
electrodeposited dioxythiophene polymers.

IT 700817-12-5P 700817-14-7P 700817-16-9P

Truong 10/728,088

Page

700817-18-lP

(prepn. of soln. processable and electrochromic
dioxythiophene-based polymers)
RN 700817-12-5 HCA

CN 2H-Thieno [3, 4-b] [ 1 , 4 ] dioxepin, 6, 8-dibromo-3, 3-dihexyl-3, 4-dihydro-
homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 700817-04-5

CMF CI 9 H30 Br2 02 S

RN 700817-14-7 HCA

CN 2H-Thieno[3,4-b] [1, 4]dioxepin, 6, 8-dibromo-3, 3-bis (2-ethylhexyl) -3,
dihydro-, homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 700817-06-7

CMF C23 H38 Br2 02 S

n-Bu- CH
Et

RN 700817-16-9 HCA

CN 2H-Thieno[3,4-b] [l,4]dioxepin, 6, 8-dibromo-3, 3-bis [ [ (2-

ethylhexyl) oxy] methyl] -3, 4-dihydro-, homopolymer {9CI) (CA INDEX

Br

Et

Br

NAME)

CM 1

Truong 10/728, 088

Page 21

CRN 700817-08-9

CMF C25 H42 Br2 04 S

RN 700817-18-1 HCA

CN 2H-Thieno [3, 4-b] [ 1 , 4 ] dioxepin, 6, 8-dibromo-3, 4-clihydro-3, 3-

bis [ (octadecyloxy) methyl] homopplymer (9CI) (CA INDEX NAME)

.CM 1

CRN 700817-10-3

CMF C45 H82 Br2 04 S

Me- (CH2) 17-0-CH2 ^ 0>

Me- (CH2).17-0-CH2

IT Alkoxylation

(Williamson; in prepn. of monomers for soln. processable and

electrochromic dioxythiophene-based polymers)
IT Bromination

Transesterif ication

(in prepn. of monomers for soln. processable and electrochromic

dioxythiophene-based polymers)
IT Polymerization

(metathetic; in prepn. of soln. processable and electrochromic

dioxythiophene-based polymers)
IT Optical switching

(of electrochromic dioxythiophene-based polymers)
IT Molecular weight

(of soln. processable and electrochromic dioxythiophene-based

Truong 10/728, 088

Page 22

polymers)
IT Conducting polymers

(polythiophenes; prepn. of soln. processable and electrochromic

dioxythiophene-based polymers)
IT. Electrochromic materials

(prepn. of soln. processable and dioxythiophene-based polymers

for electrochromic materials)
IT 128-08-5, N-Bromosuccinimide

(in prepn. of monomers for soln. processable and electrochromic

dioxythiophene-based polymers)
IT 51792-34-8, 3, 4-Dimethoxythiophene 54662-33-8 57355-20-1

700816- 90-6 700816-93-9

(in prepn. of soln. processable and electrochromic

dioxythiophene-based polymers)
IT 634 591-75-6P 634591-77-8P 70081 6-98-4P 700817-00- IP

(in prepn. of soln. processable and electrochromic

dioxythiophene-based polymers)
IT 700817-04-5P 700817-06-7P 700817-08-9P 700817-10-3P

(monomer; in prepn. of soln. processable and electrochromic

dioxythiophene-based polymers)
IT 700817-12-5P 700817-14-7P 700817-16-9P

700817- 18-lP

(prepn. of soln. processable and ele.ctrochromic
dioxythiophene-based polymers)

L26 ANSWER 7 OF 29 HCA COPYRIGHT 2005 ACS on STN

140:77531 Solid-State Synthesis of a Conducting Polythiophene via an
Unprecedented Heterocyclic Coupling Reaction. Meng, Hong;
Perepichka, Dmitrii F. ; Bendikov, Michael; Wudl, Fred; Pan, Grant
Z.; Yu, Wenjiang; Dong, Wenjian; Brown, Stuart (Department of
Chemistry and Biochemistry and the Exotic Materials Institute,
Microfabrication Lab, Department of Physics and Astrophysics,
University of California, Los Angeles, CA, 90095-1569, USA) .
Journal of the American Chemical Society, 125(49), 15151-15162
(English) 2003. CODEN: JACSAT. ISSN: 0002-7863. Publisher:
American Chemical Society.

AB Prolonged storage (.apprx.2 yr) or gentle heating (50-80 ""C)

of cryst. 2, 5-dibromo-3, 4-ethylenedioxythiophene (DBEDOT) affords a
highly conducting, bromine-doped poly (3, 4-ethylenedioxythiophene )
(PEDOT), as confirmed by solid-state NMR, FTIR, CV, and vis-NIR
spectroscopies. The novel solid-state polymn. (SSP) does not occur
for 2, 5-dichloro-3, 4-ethylenedioxythiophene (DCEDOT) , and requires a
much higher temp. (>130 ""C) for 2, 5-diiodo-3, 4-
ethylenedioxythiophene (DIEDOT) . X-ray structural anal, of the
above dihalothiophenes reveals short Hal- • -Hal

distances between adjacent mols. in DBEDOT and DIEDOT, but not in
DCEDOT. The polymn. may also occur in the melt but is significantly
slower and leads to poorly conductive material. Detailed studies of

Truong 10/728, 088

Page

the reaction were performed using ESR, DSC, microscopy, and
gravimetric analyses. SSP starts on crystal defect sites; it is
exothermic by 14 kcal/mol and requires activation energy of
.apprx.26 kcal/mol (for DBEDOT) . The temp, dependence of the cond.
of SSP-PEDOT (art = 20-80 S/cm) reveals a slight thermal
activation. It can be further increased by a factor of 2 by doping
with iodine. Using this approach, thin films of PEDOT with cond. a
high as 20 S/cm were fabricated on insulating flexible plastic
surfaces.

IT 350037-71-7P, 2, 5-Dibromo-3, 4-Ethylenedioxythiophene
homopolymer

(solid-state synthesis of conducting polythiophenes via
unprecedented heterocyclic coupling reaction)
RN 350037-71-7 HCA

CN Thienp [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2, 3-dihydro-, homopolymer
(9CI) (CA INDEX NAME)

CM 1

CRN 174508-31-7
CMF C6 H4 Br2 02 S

Br

IT NMR spectroscopy

(carbon-13, solid state; solid-state synthesis of conducting

polythiophenes via unprecedented heterocyclic coupling reaction)
IT Polymer morphology

(cryst.; solid-state synthesis of conducting polythiophenes via

unprecedented heterocyclic coupling reaction)
IT Conducting polymers

(polythiophenes; solid-state synthesis of conducting

polythiophenes via unprecedented heterocyclic coupling reaction)
IT Electric conductivity

(solid-state synthesis of conducting polythiophenes via

unprecedented heterocyclic coupling reaction)
IT 225518-49-OP, 2, 5-Dichloro-3, 4-Ethylenedioxythiophene 640737-72-C
(solid-state synthesis of conducting polythiophenes via

unprecedented heterocyclic coupling reaction)
IT 350037-71-7P, 2, 5-Dibromo-3, 4-Ethylenedioxythiophene
homopolymer

Truong 10/728, 088

Page 24

(solid-state synthesis of conducting polythiophenes via
unprecedented heterocyclic coupling reaction)
IT 174508-31-7P, 2 , 5-Dibromo-3, 4-Ethylenedioxythiophene - 640737-73-lP
(solid-state synthesis of conducting polythiophenes via
unprecedented heterocyclic coupling reaction)
IT . 109-72-8, n-Butyl lithium, reactions 128-08-5, N-Bromosuccinimide
128-09-6, N-Chlorosuccinimide 1600-27-7, Mercuric acetate
7553-56-2, Iodine, reactions 126213-50-1, 3,4-
Ethylenedioxythiophene

(solid-state synthesis of conducting polythiophenes via
unprecedented heterocyclic coupling reaction)

L26 ANSWER 8 OF 29 HCA COPYRIGHT 2005 ACS on STN

139:133926 Synthesis and electroluminescent properties of copolymers
derived from fluorene and thiophene derivatives. Hou, Q.; Niu, Y.
H.; Huang, W. B,; Yang, w;; Yang, R. Q.; Yuan, M.; Cao, Y.
(Institute of Polymer Optoelectronic Materials and Devices, South
China University of Technology, Canton, 510640, Peop. Rep. China) .
Synthetic Metals, 135-136, 185-186 (English) 2003. CODEN: SYMEDZ.
ISSN: 0379-6779. Publisher: Elsevier Science B.V. .

AB A series of sol. conjugated polymers of 2, 7-dibromo-9, 9-

dioctylf luorene, 2, 7-bis (4,4,5, 5-tetramethyl-l , 3, 2-dioxaborolan-2-
yl) -9, 9-dioctylf luorene (DOF) s with thiophene (TOP) or
2, 5-dibromo-3, 4-ethylenedioxythiophene (EDT) were synthesized via
palladium-catalyzed Suzuki coupling reaction. The DOFs-EDT and
DOFs-TOP copolymers have comonomer ratio that is very close to the
feed ratio, have alternating DOF monomer units, and give rise to
various emission colors from bluish-green to yellow. The highest
electroluminescence (EL) quantum efficiency the copolymers is 1.8%
for DOFs-EDT and 0.45% for DOFs-TOP, as measured in test device of
ITO/polythiophene-polyf luorene/Ba/Al structure. The enhanced
quantum efficiency is of interest for application in PLED displays.

IT 569355-28-8P, 2, 7-Bis (4,4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-

2-yl) -9, 9-dioctylf luorene-2, 5-dibromo-3, 4-ethylenedioxythiophene-2, 7-
dibromo-9, 9-dioctylf luorene copolymer

(prepn. of sol. conjugated polythiophene-polyf luorenes with high
electroluminescence quantum efficiency)

RN 569355-28-8 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2, 3-dihydro-, polymer with
2, 7-dibromo-9, 9-dioctyl-9H-f luorene and 2 , 2 ' - ( 9, 9-dioctyl-9H-
fluorene-2, 7-diyl)bis [4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolane] (9CI)
(CA INDEX NAME)

CM 1

CRN 198964-46-4
CMF C29 H40 Br2

Truong 10/728,088

Page 25

Me- (CH2) 7
Br

(CH2) 7-Me
Br

^^^^-^^

CM 2

CRN 196207-58-6
CMF C41 H64 B2 04

Me- (CH2) 7 (CH2) 7-Me

CM 3

CRN 174508-31-7
CMF C6 H4 Br2 02 S

Br

IT Polymerization

(Suzuki coupling; prepn. of sol. conjugated polythiophene-
polyf luorenes with high electroluminescence quantum efficiency)

IT Polymers, preparation

(conjugated; prepn. of sol. conjugated polythiophene-
polyfluorenes with high electroluminescence quantum efficiency)

IT Conducting polymers

(polythiophenes; prepn. of sol. conjugated polythiophene-
polyfluorenes with high electroluminescence quantum efficiency)

IT Luminescence, electroluminescence
Optical absorption

Truong 10/728, 088

Page 2 6

Solubility

Suzuki coupling reaction

(prepn. of sol. conjugated polythiophene-polyf luorenes with high
electroluminescence quantum efficiency)
IT 569355-28-8P, 2, 7-Bis (4, 4,5, 5-tetramethyl-l, 3, 2-dioxaborolan-

2-yl) -9, 9-dioctylf luorene-2, 5-dibromo-3, 4-ethylenedioxythiophene-2, 7-

dibromo-9, 9-dioctylf luorene copolymer 569355-29-9P,

2, 7-813 (4, 4, 5, 5-tetramethyl-l, 3, 2-dioxaborolan-2-yl) -9, 9-

dioctylf luorene-2, 7-dibromo-9, 9-dioctylf luorene-2, 5-dibromothiophene

copolymer

(prepn. of sol- conjugated polythiophene-polyf luorenes with high
electroluminescence quantum efficiency)

L26 ANSWER 9 OF 29 HCA COPYRIGHT 2005 ACS on STN

139:53566 Electronic and optical properties of polyfluorene and

f luorene-based copolymers: a quantum-chemical characterization.
Cornil, J.; Gueli, I.; Dkhissi, A.; Sancho-Garcia, J. C; Hennebicq,
E.; Calbert, J. P.; Lemaur, V.; Beljonne, D.; Bredas, J. L. (Center
for Research in Molecular Electronics and Photonics, Laboratory for
Chemistry of Novel Materials, University of Mons-Hainaut , Mons,
B-7000, Belg.) . Journal of Chemical Physics, 118(14), 6615-6623
(English) 2003. CODEN: JCPSA6. ISSN: 0021-9606. Publisher:
American Institute of Physics.

AB A detailed quantum-chem. study was carried out of the electronic and
optical properties of polyfluorene chains vs. those in copolymers
cont'g. alternating fluorene and benzothiadiazole or
ethylenedioxythiophene units. The comonomer has an important role
on the excitonic properties and the efficiency of charge- and
energy-transfer processes. The choice of comonomer is thus crit. in
targeting specific optical properties while maintaining good carrier
transport properties in polyf luorenes .

IT 498358-35-3

(quantum chem. study of electronic excitation and optical band
gap of polyfluorene and f luorene-based copolymers)

RN 498358-35-3 HCA

CN Thieno[3, 4-b]-l,4-dioxin, 5, 7-dibromo-2, 3-dihydro-, polymer with
2,7-dibromo-9, 9-dihexyl-9H-fluorene (9CI) (CA INDEX NAME)

CM 1

CRN 189367-54-2
CMF C25 H32 Br2

Truong 10/728, 088

Page 27

Me- (CH2)5
Br

(CH2)5~Me
Br

CM 2

CRN 174508-31-7
CMF C6 H4 Br2 02 S

Br

IT Polymers, properties

(conjugated; quantum chem. study of electronic excitation and
optical band gap of polyfluorene and f luorene-based copolymers)
IT Conducting polymers

(polythiophenes, ethylenedioxythiophene and benzothiadiazole,
polyf luorenes; quantum chem. study of electronic excitation and
optical band gap of polyfluorene and f luorene-based copolymers)
IT Band structure

Electronic energy transfer

Excited state

Exciton

HOMO (molecular orbital)
LUMO (molecular orbital)
Triplet state

(quantum chem. study of electronic excitation and optical band
gap of polyfluorene and f luorene-based copolymers)
IT 123864-00-6 210347-52-7 498358-35-3

(quantum chem. study of electronic excitation and optical band
gap of polyfluorene and f luorene-based copolymers)

L26 ANSWER 10 OF 29 HCA COPYRIGHT 2005 ACS on STN

139:7558 New f luorene-based light-emitting copolymers. Cao, Yong; Hou,
Qiong; Niu, Yu-hua; Yang, Ren-qiang; Xu, Yi-she; Luo, Jie; Yang, Wei
(Institute of Polymer Optoelectronic Materials and Devices, South
China Univ. of Tech., Canton, 510640, Peop. Rep. China). Huanan

Truong 10/728, 088

Page 28

Ligong Daxue Xuebao, Ziran Kexueban, 30(11), 1-10 (Chinese) 2002.
CODEN: HLDKEZ. ISSN: 1000-565X. Publisher: Huanan Ligong Daxue
Xuebao Bianji Weiyuanhui.
AB A series of novel random copolymers based on 9, 9-dioctylf luorene

(DOF) and thiophene or its derivs. (ethylenedioxythiophene (EDT) , 4,
7-dithien-2-yl-2, 1, S-benzo thiadiazole (DBT) , 4,

7-dithien-2-yl-2, 1, 3-benzoselenadiazole (BTSe) ) were synthesized by
the palladium-catalyzed Suzuki coupling method. The successful
color tuning from green (490 .apprx. 560 nm) to red (628 .apprx. 718
nm) was obtained. The PL and EL quantum efficiencies of these
random copolymers are higher than those of alternating copolymers
reported by other researchers. The maximal EL quantum efficiency is
0.45% for copolymer of f luorene and thiophene, 1.8% for copolymer of
f luorene and EDT, 1.4% for copolymer of f luorene and DBT and 0.5%
for copolymers of f luorene and BTSe. This is the highest EL
external efficiency reported so far for the same f luorene-based
copolymers. The efficient energy transfer due to exciton trapping
on the narrow band-gap BTSe or DBT sites has been obsd. The results
indicate that the use of conjugated polyfluorene as wide band-gap
segment with a small amt. of narrow band-gap dopant in the polymer
main chain could provide a new way to combine high quantum
efficiency along with color tuning ability.

IT 287924-59-8

(f luorene-based light-emitting copolymers)

RN 287924-59-8 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2, 3-dihydro-, polymer with

2, 2 ' - (9, 9-dioctyl-9H-f luorene-2, 7-diyl) bis [4, 4, 5, 5-tetramethyl-l , 3, 2-
dioxaborolane] (9CI) (CA INDEX NAME)

CM 1

CRN 196207-58-6
CMF C41 H64 B2 04

Me Me

CM 2

CRN 174508-31-7
CMF C6 H4 Br2 02 S

Truong 10/728, 088

Page 29

IT HOMO (molecular orbital)
LUMO (molecular orbital)
Luminescence
Oxidation potential

(f luorene-based light-emitting copolymers)
IT 222857-62-7 287924-59-8 534591-71-4 534591-73-6
(f luorene-based light-emitting copolymers)

L26 ANSWER 11 OF 29 HCA COPYRIGHT 2005 ACS on STN

138 : 304877 3, 4-Ethylenedioxy-substituted bithiophene-alt-thiophene-S, S-
dioxide regular copolymers. Synthesis and conductive, magnetic and
luminescence properties., Berlin, Anna; Zotti, Gianni; Zecchin,
Sandro; Schiavon, Gilberto; Cocchi, Massimo; Virgili, Dalia;
Sabatini, Cristiana (Istituto CNR di Scienze e Tecnologie
Molecolari, Milan, 20133, Italy) . Journal of Materials Chemistry,
13(1), 27-33 (English) 2003. CODEN: JMACEP. ISSN: 0959-9428.
Publisher: Royal Society of Chemistry.

AB Polyconjugated regular bithiophene-alt-thiophene-S, S-dioxide
copolymers were produced by anodic coupling of variously
3, 4-ethylenedioxy-substituted 2, 5-bis (2-thienyl) thiophene-S, S-
dioxide. The polymers were characterized by cyclic voltammetry,
FTIR reflection-absorption and UV-vis spectroscopy, MALDI-TOF mass
spectroscopy, electrochem. quartz crystal microbalance, in situ ESR
and in situ cond. techniques, photo- and electro-luminescence
measurements. The regular' alternation of electron-rich and -poor
thiophene rings in the polymer chain operated by the ethylenedioxy
and S, S-dioxide moieties produces a finite window of cond.
Alkyl-protection of the p-positions of the thiophene-S, S-
dioxide ring gave low-defect and sol. oligomers which were
investigated in single-layer org. light-emitting devices (OLEDs) .
Photoluminescence quantum efficiency of .apprx.1% and external
electroluminescence quantum efficiencies of 0.01% photon/electron at
a luminance of 100 cd m-2 were obtained.

IT 174508-31-7, 2, 5-Dibromo-3, 4- (ethylenedioxy) thiophene
(oxidn. of) ,

RN 174508-31-7 HCA

CN Thieno[3,4-b]-l,4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

Truong 10/728,088

Page 30

Br

IT 511286-88-7P 511286-89-8P 511286-90-lP
511286-91-2P 511286-92-3P

(prepn. and conductive, magnetic and luminescence properties of)

RN 511286-88-7 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 5 ' - (1, l-dioxido-2, 5-

thiophenediyDbis [2, 3-dihydro-, homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 511286-81-0
CMF CI 6 H12 06 S3

RN 511286-89-8 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 5'- (3, 4-dihexyl-l, l-dioxido-2, 5-

thiophenediyDbis [2, 3-dihydro-, homopolymer (9CI) (CA INDEX NAME)

CM 1 ■

CRN 511286-82-1
CMF C28 H36 06 S3

Me- (CH2) 5

{CH2)5-Me

Truong 10/728,088

Page 31

RN 511286-90-1 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 5.'- (3, 4-didodecyl-l, l-dioxido-2, 5-

thiophenediyDbis [2, 3-dihydro-, homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 511286-83-2
CMF C40 H60 06 S3

Me- (CH2) 11

(CH2) ll-Me

RN 511286-91-2 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 2, 3-dihydro-5, 7-di-2-thienyl-,
6,6-dioxide, homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 511286-84-3
CMF C14 HIO 04 S3

CN 5,5' :7',5' ' -Terthieno [3, 4-b] -1, 4-dioxin, 2, 2', 2' ',3, 3', 3' ' -hexahydro-
, 6' , 6' -dioxide, homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 511286-85-4
CMF C18 H14 08 S3

Truong 10/728, 088

Page 32

IT 511286-87-6P

(prepn. and reaction with ( tributylstannyl ) thiophene)
RN 511286-87-6 HCA

CN Thieno [3, 4-b] -1, 4-ciioxin, 5, 7-clibromo-2, 3-dihydro-, 6, 6-dioxide
(9CI) (CA INDEX NAME)

IT Oxidation potential

Reduction potential

(of ethylenedioxy-substituted bis (thienyl) thiophene dioxide
monomers and polymers)
IT Electric conductivity
Luminescence

Luminescence, electroluminescence

(prepn. and conductive, magnetic and luminescence properties of

ethylenedioxy-substituted bithiophene-alt-thiophene dioxide

polymers)
IT Electroluminescent devices

(single-layer electroluminescence devices prepd. from

ethylenedioxy-substituted bithiophene-alt-thiophene dioxide

polymers)
IT Polycarbonates, properties

(single-layer electroluminescence devices prepd. from

ethylenedioxy-substituted bithiophene-alt-thiophene dioxide

polymers and)
IT 25037-45-0, Bisphenol A polycarbonate

(assumed monomers; single-layer electroluminescence devices

Truong 10/728, 088

Page 33

prepd. from ethylenedioxy-substituted bithiophene-alt-thiophene
dioxide polymers and)
IT 174508-31-7, 2, 5-Dibromo-3, 4- (ethylenedioxy) thiophene
174509-52-5
(oxidn, of)

IT 511286-88-7P 511286-89-8P 511286-90-lP
511286-91-2P 511286-92-3P

(prepn, and conductive, magnetic and luminescence properties of)
IT 51128 6-81-OP 511286-82-lP 511286-83-2P 5112 8 6-84-3P
511286-85-4P

(prepn, and polymn. of)
IT 511286-86-5P

(prepn. and reaction with (tributylstannyl) (ethylenedioxy) thiophe
ne)

IT 511286-87-6P

(prepn. and reaction with (tributylstannyl) thiophene)
IT 89088-95-9, 2 , 5-Dibromothiophene-l , 1-dioxide *

(reaction with (tributylstannyl) (ethylenedioxy) thiophene)
IT 175922-79-9, 2- (Tributylstannyl) -3, 4- (ethylenedioxy) thiophene

(reaction with dibromothiophene dioxide)
IT 24936-68-3, Bisphenol A polycarbonate, sru, properties 65181-78-4,
N,N*-Diphenyl-N,N'-bis (3-methylphenyl ) -1, 1 ' -biphenyl-4 , 4 ' -diamine

(single-layer electroluminescence devices prepd. from

ethylenedioxy-substituted bithiophene-alt- thiophene dioxide

polymers and)

L26 . ANSWER 12 OF 29 HCA COPYRIGHT 2005 ACS on STN

138:288055 Facile solid-state synthesis of highly conducting

poly (ethylenedioxythiophene) . Meng, Hong; Perepichka, Dmitrii F,;
Wudl, Fred (Department of Chemistry and Biochemistry and Exotic
Materials Institute, University of California, Los Angeles, CA,
90095-1569, USA). Angewandte Chemie, International Edition, 42(6),
658-661 (English) 2003, CODEN: ACIEF5. ISSN: 1433-7851.
Publisher: Wiley-VCH Verlag GmbH & Co. KGaA.

AB The prepn. of PEDOT by catalyst-free coupling polymn. of

2, 5-dibromo-3, 4-ethylenedioxythiophene in the solid state at
accelerated temps. (60, 80, and 120"") is reported. The cond.
of polymer films on plastic and glass substrate was examd. Crystal
structure data for the monomer are presented.

IT 163359-60-2P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene
homopolymer, SRU 350037-71-7P, 2 , 5-Dibromo-3, 4-
ethylenedioxy thiophene homopolymer

(solid-state polymn. of dibromoethylenedioxythiophene and cond.
of poly (ethylenedioxythiophene) )

RN 163359-60-2 HCA

CN Poly (2, 3-dihydrothieno [3, 4-b] -1, 4-dioxin-5, 7-diyl) (9CI) (CA INDEX
NAME)

Truong 10/728,088

Page 34

n

RN 350037-71-7 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2, 3-dihydro-, homopolymer
(9CI) (CA INDEX NAME)

CM 1

CRN 174508-31-7
CMF C6 H4 Br 2 02 S

IT 174508-31-7, 2, 5-Dibromo-3, 4-ethylenedioxythiophene

(structure and solid-state polymn. of

dibromoethylenedioxythiophene)
RN 174508-31-7 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX

NAME)

Br

Polymer morphology

Truong 10/728, 088

Page 35

(cryst./ solid-state polymn. of dibromoethylenedioxythiophene and

cond. of poly (ethylenedioxythiophene) )
IT Crystal structure

(of 2, 5-dibromo-3, 4-ethylenedioxythiophene)
IT Conducting polymers

Electric conductivity

(solid-state polymn. of dibromoethylenedioxythiophene and cond.

of poly (ethylenedioxythiophene) )
IT 163359-60-2P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene
homopolymer, SRU 350037-71-7P, 2 , 5-Dibromo-3, 4-
ethylenedioxythiophene homopolymer

(solid-state polymn. of dibromoethylenedioxythiophene and cond.

of poly (ethylenedioxythiophene) )
IT 174508-31-7, 2, 5-Dibromo-3, 4-ethylenedioxythiophene

(structure and solid-state polymn. of

dibromoethylenedioxythiophene)

L26 ANSWER 13 OF 29 HCA COPYRIGHT 2005 ACS on STN

138:188206 EQCM analysis of the. alkali metal ion coordination properties
of novel poly ( thiophene) s 3, 4-functionalized with crown-ether
moieties. Berlin, A.; Zotti, G.; Zecchin, S.; Schiavon, G.
(Istituto CNR di Scienze e Tecnologie Molecolari, Milan, 20133,
Italy). Synthetic Metals, 131(1-3), 149-160 (English) 2002. CODEN:
SYMEDZ. ISSN: 0379-6779. Publisher: Elsevier Science B.V..

AB New thiophenes carrying 18-crown-6-ether ring directly linked to the
3- and 4-positions of the thiophene ring were synthesized and
polymd. by anodic coupling in acetonitrile . The polymers were
characterized by cyclic voltammetry (CV) , UV-Vis and FTIR
spectroscopy, matrix-assisted laser desorption ionization (MALDI)
mass spectroscopy and in situ cond. Electrochem. quartz crystal
microbalance (EQCM) anal, of the alkali metal coordination ability
of the 18-crown-6-ether polymer films in acetonitrile has evidenced
that the coordination consts. (e.g. 20-80 M-1 for Na+) are ca. two
orders of magnitude lower than those of polythiophenes bearing the
crown substituents pendant from the polythiophene backbone. The
result has been ascribed both to electronic and solid-state effects
of the conjugated polythiophene chains.

IT 249513-23-3P 484640-50-8P 484640-51-9P
497937-33-4P 497937-34-5P

(EQCM anal, of alkali metal ion coordination properties of
poly (thiophene) s 3, 4-f unctionalized with crown-ether moieties)

RN 249513-23-3 HCA

CN Thieno [3, 4-b] -1, 4, 7, 10-tetraoxacyclododecin, .2, 3, 5, 6, 8, 9-hexahydro-,
homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 122372-73-0

Truong 10/728,088

Page. 36

CMF CIO H14 04 S

RN 484640-50-8 HCA

CN Thieno [3, 4-b] -1,4,7, 10, 13, 16-hexaoxacyclooctadecin,
17, 19-bis (2,3-dihydrothieno[3,4-b]-l, 4-dioxin-5-yl) -
2, 3, 5, 6, 8, 9, 11, 12, 14, 15-decahydro-, homopolyiher (9CI) (CA INDEX
NAME)

CM 1

CRN 484640-48-4
CMF C26 H30 OlO S3

RN 484640-51-9 HCA

CN Thieno [3, 4-b] -1,4,7, 10, 13, 16-hexaoxacyclooctadecin,

2, 3, 5, 6, 8, 9, 11, 12, 14, 15-decahydro-17 , 19-di-2-thienyl-, homopolymer
(9CI) (CA INDEX NAME)

CM 1

CRN 484640-49-5
CMF C22 H26 06 S3

Truong 10/728,088

Page 37

RN 497937-33-4 HCA

CN Thieno [3, 4-b]-l,4,7,10,13, 16-hexaoxacyclooctadecin,

2, 3, 5, 6, 8, 9, 11, 12, 14, IS-decahydro-, homopolymer (9CI) (CA INDEX
NAME)

CM 1

CRN 122372-75-2
CMF C14 H22 06 S

RN 497937-34-5 HCA

CN 17, 17' -Bithieno [3, 4-b] -1,4,7,10, 13, 16-hexaoxacyclooctadecin,
2,2',3,3',5,5',6,5',8,8',9,9',11,11M2,12M4,14M5,15'-
eicosahydro-, homopolymer (9CI) (CA INDEX NAME)

CM 1

IT 233756-39-3P

(EQCM anal, of alkali metal ion coordination properties of

Truong 10/728, 088

Page 38

poly ( thiophene) s 3, 4-functionalized with crown-ether moieties)
RN 233756-39-3 HCA

CN Thieno [3,4-b]-l,4,7,10,13, 1 6-hexaoxacyclooctadecin,

17, 19-dibromo-2, 3, 5, 6, 8, 9, 11, 12, 14 , 15-decahydro- (9CI) (CA INDEX
NAME)

' Br

IT Cyclic voltammetry

Electric conductivity

(EQCM anal, of alkali metal ion coordination properties of
poly (thiophene) s 3, 4-functionalized with crown-ether moieties)
IT Polymerization

(electrochem. ; EQCM anal, of alkali metal ion coordination
properties of poly (thiophene) s 3, 4-functionalized with
crown-ether moieties)
IT 7439-93-2, Lithium, properties 7440-23-5, Sodium, properties
(EQCM anal, of alkali metal ion coordination properties of
poly (thiophene) s 3, 4-functionalized with crown-ether moieties)
IT 249513-23-3P 484640-50-8P 484640-51-9P
497937-33-4P 497937-34-5P

(EQCM anal, of alkali metal ion coordination properties of
poly (thiophene) s 3, 4-functionalized with crown-ether moieties)
IT 122372-7 5-2 12 6213-50-1 4 84 64 0-4 8-4 4 84 64 0-4 9-5

(EQCM anal, of alkali metal ion coordination properties of
poly (thiophene) s 3 , 4-functionalized with crown-ether moieties)
IT 233756-39-3P 4 97937-32-3P

(EQCM anal, of alkali metal ion coordination properties of
poly (thiophene) s 3, 4-functionalized with crown-ether moieties)

L26 ANSWER 14 OF 29 HCA COPYRIGHT 2005 ACS on STN

138:188177 New organic materials for light emitting devices based on
dihexyl-f luorene-co-ethylenedioxythiophene copolymers exhibiting
improved hole-injecting properties. Stephan, Olivier; Tran-Van,
Francois; Chevrot, Claude (Universite Joseph Fourier Grenoble 1 and
CNRS (UMR C5588), Laboratoire de Spectrometrie Physique, Saint
Martin d'Heres, 38402, Fr.). Synthetic Metals, 131(1-3), 31-40
(English) 2002. CODEN: SYMEDZ . ISSN: 0379-6779. Publisher:
Elsevier Science B.V, .

AB We report the synthesis, optical and electrochem. characterizations
of 9, 9-di-n-hexyl-f luorene-co-3, 4-ethylenedioxythiophene

Truong 10/728, 088

Page 39

(DHF-co-EDOT) copolymers obtained from a mixt., in various ratios,
of the two corresponding di-brominated monomers by dehalogenation
polycondensation . Elemental anal., IR studies coupled with IH NMR
clearly indicate, as expected, that the amt . of each monomer unit in
the final materials is strongly correlated with the feed compn. even
though the reactivity of the di-brominated EDOT seems lower than
that of di-brominated DHF. It appears that even a low EDOT content,
i.e. 11-15 mol%, within a PDHF main chain, leading to the copolymer
COPOl, caused significant changes in the electronic properties of
the material when compared to PDHF homopolymer. Higher EDOT
contents lead to less sol. copolymers which are not suitable for
investigation of their use as luminescent semiconducting
7i-conjugated materials in org. light emitting diodes. Green org.
light emitting devices based on COPOl have been investigated and
showed improved hole injection properties when compared to devices
based on PDHF homopolymer. The origin of the emitted light has been
attributed to the concomitant emission of aggregates PDHF segments
with EDOT short oligomeric segments. The use of an addnl .
poly (3, 4-ethylenedioxythiophene-2, 5-diyl) -polystyrene sulfonate
layer on the indium tin oxide (ITO) anode has also been investigated
and leads to improved operating lifetime.
IT 350037-71-7, 2, 5-Dibromo-3, 4-ethylenedioxythiophene
homopolymer

(improved hole-injecting properties of copolymers dihexylf luorene
with ethylenedioxythiophene)
RN 350037-71-7 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2, 3-dihydro-, homopolymer
(9CI) (CA INDEX NAME)

CM 1

CRN 174508-31-7
CMF C6 H4 Br2 02 S

Br

IT 498358-35-3P

(improved hole-injecting properties of copolymers dihexylf luorene
with ethylenedioxythiophene)
RN 498358-35-3 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2, 3-dihydro-, polymer with

Truong 10/728, 088

Page 4 0

2, 7-dibromo-9, 9-dihexyl-9H-fluorene (9CI) (CA INDEX NAME)
CM 1

CRN 189367-54-2
CMF C25 H32 Br2

Me- (CH2)5
Br

(CH2)5-Me
Br

CM 2

CRN 174508-31-7
CMF C6 H4 Br 2 02 S

Br ■

IT Polymers, preparation

(conjugated; improved hole-injecting properties of copolymers
dihexylf luorene with ethylenedioxythiophene)
IT Cyclic voltammetry
Electric current
Electroluminescent devices
Light

Luminescence

Luminescence, electroluminescence
Molecular weight distribution
Optical absorption
UV radiation

(improved hole-injecting properties of copolymers dihexylf luorene
with ethylenedioxythiophene)
IT" Thickness

(thickness effect of conducting polymer on electroluminescent
device)
IT 7440-66-6, Zinc, uses

(activated, polymn. catalyst; improved hole-injecting properties

Truong 10/728, 088

Page 41

of copolymers dihexylf luorene with ethylenedioxythiophene)
IT 163359-60-2 350037-71-7, 2, 5-Dibromo-3, 4-
ethylenedioxythiophene homopolymer

(improved hole-injecting properties of copolymers dihexylf luorene

with ethylenedioxythiophene)
IT 498358-35-3P

(improved hole-injecting properties of copolymers dihexylf luorene

with ethylenedioxythiophene)
IT 133019-09-7P, Poly (9, 9-dihexyl-9H-f luorene-2, 7-diyl) 201807-75-2P,
2, 7-Dibromo-9, 9-dihexylf luorene homopolymer

(improved hole-injecting properties of copolymers dihexylf luorene

with ethylenedioxythiophene)
IT 111-25-1, 1-Bromohexane 16433-88-8, 2, 7-Dibromof luorene

(monomer synthesis; improved hole-injecting properties of

copolymers dihexylf luorene with ethylenedioxythiophene)
IT 189367-54-2P, 2, 7-Dibromo-9, 9-di-n-hexyl-f luorene

(monomer; improved hole-injecting properties of copolymers

dihexylf luorene with ethylenedioxythiophene)
IT 603-35-0, Triphenylphosphine, uses 46389-47-3, 2,2' -Bipyridine
Nickel dibromide

(polymn. catalyst; improved hole-injecting properties of

copolymers dihexylf luorene with ethylenedioxythiophene)

L26 ANSWER 15 OF 29 HCA COPYRIGHT 2005 ACS on STN

137:85573 Dihexyl-f luorene-co-3, 4 ethylenedioxythiophene copolymers for
OLEDs. Stephan, Olivier; Tran-Van, Francois; Contat, Jerome;
Dubois, Angelique; Chevrot, Claude (Laboratoire de Spectrometrie
Physique, Universite Joseph Fourier Grenoble 1, Saint Martin
d'Heres, 38402, Fr.). Materials Research Society Symposium
Proceedings, 660 (Organic Electronic and Photonic Materials and
Devices), JJl . 5/1- JJl . 5/6 (English) 2001. CODEN: MRSPDH. ISSN:
0272-9172. Publisher: Materials Research Society.

AB The authors report synthesis, and optical properties, of

dihexyl-f luorene-co-3, 4 -ethylenedioxythiophene (DHF-co-EDOT) random
copolymers obtained from mixt., in various ratios, of the two
corresponding dibrominated monomers. IR studies coupled with IH NMR
clearly indicate, as expected, that the amt. of each monomer unit in
the materials is strongly connected to the feed compn. It clearly
appears that even a low 3, 4-ethylenedioxythiophene (EDOT) content,
i.e. 15%, within a poly(dihexyl f luorene) main chain induces
significant changes in the electronic properties of the
corresponding material, denoted COPOl, compared with the
f luorene-based homopolymer. Higher EDOT contents lead to less sol.
copolymers which are not or only to a slight extent suitable to
study their use as luminescent semiconducting 7i-conjugated
materials in Org. Light-Emitting Diodes (OLEDs) . Green org. light
emitting devices based on COPOl, exhibiting no significant spectral
evolution, were demonstrated and showed improved hole-injection

Truong 10/728, 088

Page 42

properties when compared to the ones using poly(dihexyl fluorene) .
The use of an addnl . PEDOT-PSS layer on the ITO anode also was
studied leading to improved operating lifetime.
IT 350037-71-7P

(dihexyl-f luorene-co-3, 4 ethylenedioxythiophene copolymers for
OLEDs)
RN 350037-71-7 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2/ 3-dihydro-, homopolymer
(9CI) (CA INDEX NAME)

CM 1

CRN 174508-31-7
CMF C6 H4 Br2 02 S

Br

IT Electroluminescent devices

(org.; dihexyl-f luorene-co-3, 4 ethylenedioxythiophene copolymers

for OLEDs)
IT NMR (nuclear magnetic resonance)

(proton; dihexyl-f luorene-co-3, 4 ethylenedioxythiophene

copolymers for OLEDs)
IT 7429-90-5, Aluminum, uses 50926-11-9, Indium tin oxide

(dihexyl-f luorene-co-3, 4 ethylenedioxythiophene copolymers for

OLEDs)

IT 12 6213-51-2P, PEDOT 13818 4-36-8P 201807-75-2P
350037-71-7P 40398 6-27- 6P

(dihexyl-f luorene-co-3, 4 ethylenedioxythiophene copolymers for

OLEDs)

IT 50851-57-5 123863-98-9, Poly ( 9, 9-dihexylf luorene )

(dihexyl-f luorene-co-3, 4 ethylenedioxythiophene copolymers for
OLEDs)

L26 ANSWER 16 OF 29 HCA COPYRIGHT 2005 ACS on STN

137:20713 Vinylene-linked donor-acceptor polymers. Madrigal, Luis G.;
Pinto, Mauricio; Schanze, Kirk S.; Reynolds, John R. (Dep. Chem.,
Center Macromolecular Sci. Eng., Univ. Florida, Gainesville, FL,
32611, USA) . Polymer Preprints (American Chemical Society, Division
of Polymer Chemistry), 43(1), 565 (English) 2002. CODEN: ACPPAY.
ISSN: 0032-3934. Publisher: American Chemical Society, Division of

Truong 10/728, 088

Page 43

Polymer Chemistry.

AB Vinylene-^linked donor-acceptor polymers were synthesized to obtain
materials with low electronic band gap and accessible oxidative and
reductive states. The Heck reaction was used to prep,
poly (2, 5-pyridyl vinylene-l, 4-hexadecyloxy-phenylene vinylene) (PI) ,
poly (2, 3-diphenyl [3, 4-b] -pyridopyrazine vinylene-1, 4-hexadecyloxy
phenylene vinylene) (P2) , and poly (propylenedioxythiophene-MeOCl 6H33
vinylene-1 , 4-pyridyl vinylene) (P3) . The polyphenylenevinylenes
exhibit optical band gap of 2.4, 2.0, and 2.4 eV resp. The mol.,wt.
of these sol. polymers is 8,700 to 33,000 g/mol as detd. by GPC vs.
polystyrene std. Doping of the polymers with antimony pentachloride
led to formation of new red-shifted optical absorption bands
characteristic of charge transfer species. A small pos.
solvatochromism was obsd. from fluorescence spectra in solvents with
distinct polarity but nearly the same Hildebrand soly. parameter; a
relatively large Stokes-shift was also obsd.

IT 434935-11-2P

(prepn. and optical band gap and solvatochromism of fluorescent
vinylene-linked pyridyl- and pyridopyrazine- and
propylenedioxythiophene-contg. donor-acceptor conjugated
polymers)

RN 434935-11-2 HCA

CN Pyridine, 2, 5-diethenyl-, polymer with 6, 8-dibromo-3, 3-

bis (hexadecyloxy) -3, 4-dihydro-2H-thieno [3, 4-b] [1, 4]dioxepin (9CI)
(CA INDEX NAME)

CM 1

CRN 434935-10-1

CMF C39 H70 Br2 04 S

Br

Me- (CH2) 15-0,
Me- {CH2) 15-

0,

Br

CM 2

CRN 16222-95-0
CMF C9 H9 N

Truong 10/728, 088

Page 4 4

E2C= CH N

^^^^^^^ CH= CH2

IT Polymers, preparation

(conjugated; prepn. and optical band gap and solvatochromism of
fluorescent vinylene-linked pyridyl- and pyridopyrazine- and
propylenedioxythiophene-contg. donor-acceptor conjugated
polymers)

IT Band gap

(optical; prepn. and optical band gap and solvatochromism of
fluorescent vinylene-linked pyridyl- and pyridopyrazine- and
propylenedioxythiophene-contg. donor-acceptor conjugated
polymers)
IT Conducting polymers

(polythiophenes, pyridyl-contg . ; prepn. and optical band gap and
solvatochromism of fluorescent vinylene-linked pyridyl- and
pyridopyrazine- and propylenedioxythiophene-contg. donor-acceptor
conjugated polymers)
IT Charge transfer interaction
Excited state absorption
Optical absorption edge
Polarized fluorescence
Solvatochromism

(prepn. and optical band gap and solvatochromism of fluorescent
vinylene-linked pyridyl- and pyridopyrazine- and
propylenedioxythiophene-contg. donor-acceptor conjugated
polymers)

IT Poly (arylenealkenylenes)

(pyridyl and pyridopyrazine contg.; prepn. and optical band gap
and solvatochromism of fluorescent vinylene-linked pyridyl- and
pyridopyrazine- and propylenedioxythiophene-contg. donor-acceptor
conjugated polymers)

IT 7647-18-9, Antimony pentachloride

(dopant; prepn. and- optical band gap and solvatochromism of
fluorescent vinylene-linked pyridyl- and pyridopyrazine- and
propylenedioxythiophene-contg . donor-acceptor conjugated
polymers)

IT 178667-14-6P 178900-73-7P 434935-09-8P 434935-11-2P

434 94 3-0 9- 6P 4 34 94 3-10-9P

(prepn. and optical band gap and solvatochromism of fluorescent
vinylene-linked pyridyl- and pyridopyrazine- and
propylenedioxythiophene-contg . donor-acceptor con j ugated
polymers)

Truong 10/728, 088

Page 45

IT 108-94-1, Cyclohexanone, uses

(solvent; prepn. and optical band gap and solvatochromism of
fluorescent vinylene-linked pyridyl- and pyridopyrazine- and
propylenedioxythiophene-contg . donor-acceptor con j ugated
polymers)

L26 ANSWER 17 OF 29 HCA COPYRIGHT 2005 ACS on STN
136:200547 Neutral poly (3, 4-ethylenedioxythiophene-2, 5-diyl) s:

preparation by organometallic polycondensation and their unique
p-doping behavior. Yamamoto, Takakazu; Shiraishi, Kouichi; Abla,
Mahmut; Yamaguchi, Isao; Groenendaal, L. "Bert" (Chemical Resources
Laboratory, Tokyo Institute of Technology, Yokohama, Midori-ku,
226-8503, Japan). Polymer, Volume Date 2002, 43(3), 711-719
(English) 2001. CODEN: POLMAG. ISSN: 0032-3861. Publisher:
Elsevier Science Ltd. .
AB Neutral and non-doped poly (3, 4-ethylenedioxythiophene) , PEDOTh(Ni),
and its hexyl deriv., PED0Th-C6 (Ni ) , have been prepd. by
organometallic dehalogenation polycondensation of

2, 5-dichloro-3, 4-ethylenedioxythiophene and its hexyl deriv. with a
zerovalent nickel complex. PED0Th-C6 (Ni ) was sol. in org. solvents
and IH NMR data indicated that it had an Mn of 11,000. MALDI-TOF
mass anal, of PEDOTh(Ni) gave Mn and Mw of about 1700 and 2400,
resp. PED0Th-C6 (Ni) showed a UV-Vis absorption peak at 546 nm in
CHC13. Electrochem. oxidn. of PED0Th-C6 (Ni ) started at about -0.40
V vs Ag+/Ag and gave a peak at 0.20 V vs Ag+/Ag. Chem. and
electrochem. oxidn. (or p-doping) of PED0Th-C6 (Ni) , both in solns.
and in a solid state, led to weakening of the original tt-ti*
peaks and rise of new peak(s) in a region of 800-1500 nm. The
p-doping of PED0Th-C6 (Ni) caused not only a decrease in the
intensity of IH NMR signals of the bridging ethylene hydrogens but
also a decrease in that of the hexyl side chain, suggesting a strong
interaction of the p-dopant with the side chain. NMR data of
poly (3-methoxythiophene-2, 5-diyl) also supported an assumption that
p-doping brings about a severe change in electronic state of the
substituent attached to the polythiophene main chain. PEDOTh(Ni)
had a d. of 1.71 g cm-3; the mol. packing mode of PEDOTh(Ni) is
discussed based on the d. of the polymer and its XRD data.
IT 163359-60-2P 225518-50-3P 350827-43-9P

(prepn. of neutral poly (ethylenedioxythiophenediyl) s by
organometallic polycondensation and their unique p-doping
behavior)
RN 163359-60-2 HCA

CN Poly (2, 3-dihydrothieno [3, 4-b] -1, 4-dioxin-5, 7-diyl) (9CI) (CA INDEX
NAME)

Page 4 6

RN 225518-50-3 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-ciichloro-2, 3-ciihydro-, homopolymer
{9CI) (CA INDEX NAME)

CM 1

CRN 225518-49-0
CMF C6 H4 C12 02 S

RN 350827-43-9 HCA

CN Thieno [3, 4-b] -1/ 4-dioxin, 5, 7-dichloro-2-hexyl-2, 3-dihydro-,
homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 350827-42-8

CMF C12 HI 6 C12 02 S

Truong 10/728,088

Page 47

CI

Me- (CH2)5

CI

IT- 225518-49-OP 35Q827-42-8P

(prepn. of neutral poly (ethylenedioxythiophenediyl) s by
organometallic polycondensation and their unique p-doping
behavior)

RN 225518-49-0 HCA

CN Thieno[3,4-b]-l,4-dioxin, 5, 7-dichloro-2, 3-dihydro- (9CI) (CA INDEX
NAME)

CI

RN 350827-42-8 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dichloro-2-hexyl-2, 3-dihydro- (9CI)
(CA INDEX NAME)

CI

Me- (CH2)5

\

CI

IT Electric conductivity

(prepn. of neutral poly (ethylenedioxythiophenediyl) s by
organometallic polycondensation and their unique p-doping

behavior)

IT 163359-60-2P 225518-50-3P 350827-43-9P
351317-30-lP

(prepn. of neutral poly (ethylenedioxythiophenediyl ) s by
organometallic polycondensation and their unique p-doping

Truong 10/728, 088

Page 4 8

behavior)
IT 126213-50-1 12 6213-53-4

(prepn. of neutral poly (ethylenedioxythiophenediyl ) s by

organometallic polycondensation and their unique p-doping

behavior)
IT 2255i8-49-0P 350827-42-8P

(prepn. of neutral poly (ethylenedioxythiophenediyl ) s by

organometallic polycondensation and their unique p-doping

behavior)

L26 ANSWER 18 OF 29 HCA COPYRIGHT 2005 ACS on STN
135:242592 Optical and electrochemical properties of soluble

N-hexylcarbazole-co-3, 4-ethylenedioxythiophene copolymers . Beouch,
L.; Tran Van, F.; Stephan, 0.; Vial, J. C; Chevrot, C. (Equipe
Reactivite aux Interfaces (EA 2528), Laboratoire sur les Polymeres
et les Materiaux Electroactif s, Universite de Cergy Pontoise, Cergy
Pontoise, 95013, Fr.). Synthetic Metals, 122(2), 351-358 (English)
2001. CODEN: SYMEDZ . ISSN: 0379-6779. Publisher; Elsevier Science
S • A. • .

AB Sol . N-hexylcarbazole-co-3, 4-ethylenedioxythiophene (HCz-co-EDOT )
copolymers from mixts. in various ratio of the two corresponding
dihalogenated monomers were synthesized. The random copolymers were
obtained from EDOT/HCz starting molar ratio: 0.25, 1, 4, named,
resp., CI, C2 and C3, and compared their properties to the two
homopolymers synthesized in the same way. The IR studies clearly
indicated, that an increase in the amt. of ethylenedioxythiophene in
the feed compn. leads to an increase of the proportion of the
corresponding comonomer in the final materials. Elemental anal,
point out that the reactivity of dibrominated EDOT seems slightly
lower than that of dibrominated HCz, Thin films of copolymer have
been prepd. and their electrochem. response have been investigated.
Absorption and luminescence of these- materials have been also
studied in CHC13. Copolymers mainly composed of one monomer (CI and
C3) behaves like the corresponding homopolymers. On an other hand,
copolymer (C2) obtained from an equimolar amt. of each monomer in
the feed compn. clearly exhibits distinct signals in optical spectra
and in electrochem. behavior, probably due to the presence of each
monomer unit short segments . The use of C2 has been explored for
possible application in light emitting devices indicating that the
p-doping of the material would be facilitated leading, to an improved
hole injecting when compared to carbazole homopolymer. It could be
particularly interesting as a hole transporting layer in multilayer
org. light emitting devices.

IT 163359-60-2P 350037-71-7P 359829-16-6P

(optical and electrochem. properties of sol. N-hexylcarbazole-co-
3, 4-ethylenedioxythiophene copolymers)

RN 163359-60-2 HCA

CN Poly (2, 3-dihydrothieno[3, 4-b] -1, 4-dioxin-5, 7-diyl) (9CI) (CA INDEX

Truong 10/728,088

Page

NAME)

RN 350037-71-7 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2, 3-dihydro-, homopolymer
(9CI) (CA INDEX NAME)

CM 1

CRN 174508-31-7
CMF C6 H4 Br2 02 S

RN 359829-16-6 HCA

CN 9H-Carbazole, 3, 6-dibromo-9-hexyl-, polymer with

5, 7-dibromo-2, 3-dihydrothieno [3, 4-b] -1, 4-dioxin (9CI)
NAME)

(CA INDEX

CM

CRN 174508-31-7
CMF C6 H4 Br2 02 S

Truong 10/728,088

Page 50

CM 2 '

CRN 150623-72-6
CMF C18 H19 Br2 N

(CH2)5-Me

IT 174508-31-7P

(optical and electrochem. properties of sol. N-hexylcarbazole-co-
3, 4-ethyleneciioxythiophene copolymers)
RN 174508-31-7 HCA

CN Thieno[3,4-b]"l,4-dioxin, 5, 7-dibroino-2, 3-dihydro- (9CI) (CA INDEX
NAME)

Br

IT Absorption spectra
Cyclic voltammetry
Fluorescence
Hole transport
Luminescence

Luminescence, electroluminescence

(optical and electrochem. properties of sol. N-hexylcarbazole-co-

Truong 10/728, 088

Page 51

3, 4-ethylenedioxythiophene copolymers)
IT Band gap

(optical; optical and electrochein. properties of sol.

N-hexylcarbazole-co-3, 4-ethylenedioxythiophene copolymers)
IT Polymers, preparation

(polythiophenes, carbazole group-contg . ; optical and electrochem.

properties of sol. N-hexylcarbazole-co-3, 4-ethylenedioxythiophene

copolymers)
IT 7440-66-6, Zinc, uses

(activated; optical and electrochem. properties of sol.

N-hexylcarbazole-co-3, 4-ethylenedioxythiophene copolymers)
IT 56-37-1, Triethylbenzylammonium chloride

(optical and electrochem. properties of sol. N-hexylcarbazole-co-

3, 4-ethylenedioxythiophene copolymers)
IT 163359-60-2P 350037-71-7P 359829-15-5P

359829-16-6P 359829-17-7P, Poly (9-hexyl-9H-carbazole-3, 6-
diyl)

(optical and electrochem. properties of sol. N-hexylcarbazole-co-

3, 4-ethylenedioxythiophene copolymers)
IT 111-25-1, Hexyl bromide 128-08-5, N-Bromosuccinimide 6825-20-3,
3, 6-Dibromocarbazole 126213-50-1, 3, 4-Ethylenedioxythiophene

(optical and electrochem. properties of sol. N-hexylcarbazole-co-

3, 4-ethylenedioxythiophene copolymers)
IT 150623-72-6P 174508-31-7P

(optical and - electrochem. properties of sol. N-hexylcarbazole-co-

3, 4-ethylenedioxythiophene copolymers)
IT 46389-47-3, 2, 2 ' -Bipyridinenickel dibromide

(polymn. catalyst; optical and electrochem, properties of sol.

N-hexylcarbazole-co-3, 4-ethylenedioxythiophene copolymers)

L26 ANSWER 19 OF 29 HCA COPYRIGHT 2005 ACS on STN

135:122840 Preparation of a soluble and neutral alkyl derivative of
poly (3, 4-ethylene-dioxythiophene) and its optical properties.
Shiraishi, K.; Kanbara, T.; Yamamoto, T.; Groenendaal, L. B.
(Chemical Resources Laboratory, Tokyo Institute of Technology,
Nagatsuta, Midori-ku, Yokohama, 226-8503, Japan). Polymer, 42(16),
7229-7232 (English) 2001. CODEN: POLMAG. ISSN: 0032-3861.
Publisher: Elsevier Science Ltd..

AB Sol. and non-doped poly (3, 4-ethylenedioxythiophene) with a hexyl

substituent (PED0Th~C6 (Ni)), was first synthesized by Ni promoted
dehalogenation polycondensation of the corresponding monomer.
PED0Th-C6 (Ni) exhibited good soly. in common org, solvents such as
CHC13, CH2C12, and DMF, in contrast to poor soly. of the
corresponding polymer synthesized by oxidative polymn. GPC anal,
indicated that PED0Th-C6 (Ni) had Mn and Mw of 5400 and 8500 (vs
polystyrene stds.); IH NMR anal, gave an Mn value of 11,000. A cast
film of PED0Th-C6 (Ni) received electrochem. p-doping at 0.20 V vs
Ag+/Ag. Chem. and electrochem. oxidn. of PED0Th-C6 (Ni) led to

Truong 10/728, 088

Page 52

appearance of new absorption bands in the near IR region.

IT 350827-43-9P

(prepn. of a sol, and neutral hexyl deriv. of
poly (3, 4-ethylene-dioxythiophene) and optical properties of
nondoped and doped polymers)

RN 350827-43-9 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dichloro-2-hexyl-2, 3-dihydro-,
homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 350827-42-8

CMF C12 H16 C12 02 S

IT Dopants
Doping

UV and visible spectra

(prepn. of a sol. and neutral hexyl deriv. of
poly (3, 4-ethylene-dioxythiophene) and optical properties of
nondoped and doped polymers)

IT 7553-56-2, Iodine, uses

(dopant; prepn. of a sol. and neutral hexyl deriv. of
poly (3, 4-ethylene-dioxythiophene) and optical properties of
nondoped and doped polymers)

IT 350827-42-8P

(monomer; prepn. of a sol. and neutral hexyl deriv. of
poly (3, 4-ethylene-dioxythiophene) and optical properties of
nondoped and doped polymers)

IT 12 95-35-8, Bis (1, 5-cyclooctadiene) nickel

(polymn. catalyst; prepn. of a sol. and neutral hexyl deriv. of
poly (3, 4-ethylene-dioxythiophene) and optical properties of
nondoped and doped polymers)

IT 350827-43-9P 351317-30-lP

(prepn. of a sol. and neutral hexyl deriv. of
poly (3, 4-ethylene-dioxythiophene) and optical properties of
nondoped and doped polymers)

IT 128-09-6, N-Chlorosuccinimide

(reactant in monomer prepn.; prepn. of a sol. and neutral hexyl
deriv. of poly (3, 4-ethylene-dioxythiophene) and optical

Truong 10/728,088

Page 53

L26
135

AB

IT

RN
CN

properties of nondoped and doped polymers)
\

ANSWER 20 OF 29 HCA COPYRIGHT 2005 ACS on STN
108027 A fully undoped oligo (3, 4~ethylenedioxythiophene) :
spectroscopic properties. Tran-Van, F.; Garreau, S.; Louarn, G,;
Froyer, G.; Chevrot, C. (Laboratoire sur les Polymeres et les
Materiaux Electroactif s, 5 mail Gay Lussac, Universite de Cergy
Pontoise, Cerg^y Pontoise, 95013, Fr.). Synthetic Metals, 119(1-3),
381-382 (English) 2001. CODEN: SYMEDZ . ISSN: 0379-6779.
Publisher: Elsevier Science S.A..

We present hereVihe synthesis of fully undoped oligo(3,4-
ethylenedioxythio^phene) by a dehalogenation polycondensation route.
Since it is partly sol., spectroscopic expts. like optical
absorption were carried out. The oligomer was studied by means of
Raman scattering, IR absorption and x-ray diffraction, and compared
to the PEDOT obtained by oxidative way.
350037-

If

obtained
■71-7DP, debrc}minated
(prepn. and specti^oscopic characterization of)

:ros

350037-71-7 HCA
Thieno [3, 4-b] -1, 4-dioxin,
(9CI) (CA INDEX NAME]*

5, 7-dibromo-2, 3-dihydro-, homopolymer

CM 1

CRN 174508-31-7
CMF C6 H4 Br2 02

IT 350037-71-7DP, debrominated

(prepn. and spectroscopic characterization of)

L2 6 ANSWER 21 OF 2 9 HCA COPYRIGHT 2005 ACS on STN

135:107664 Fully undoped and soluble oligo ( 3, 4-ethylenedioxythiophene) s :
spectroscopic study and electrochemical characterization. Tran-Van,
Francois; Garreau, Sebastian; Louarn, Guy; Froyer, Gerard; Chevrot,
Claude (Equipe Reactivite aux Interfaces (EA 2528), Laboratoire sur
les Polymeres et les Materiaux Electroactif s, Universite de Cergy
Pontoise, Cergy Pontoise, 95013, Fr.). Journal of Materials
Chemistry, 11(5), 1378-1382 (English) 2001. CODEN: JMACEP. ISSN:
0959-9428. Publisher: Royal Society of Chemistry.

Truong 10/728, 088

Page 54

AB Fully undoped oligo (3, 4-ethylenedioxythiophene) s were synthesized
via polycondensation of the dibromo monomer in the presence of
NiBr2 (bpy) catalyst in N, N-dimethylacetamide (DMA). HPLC anal,
indicated that the material is constituted of three main oligomers
which were clearly detected by UV-Visible spectroscopy. The
polythiophenes are partially sol. in DMA making them easier to
process to produce thin films of oligomers by evapn. of the solvent.
Electrochem. and electrochromic properties of undoped films were
studied. Deep purple in its undoped state, the material becomes sky
blue in the oxidized form. The mixt. of oligomers was characterized
by Raman scattering, IR absorption and X-Ray diffraction, and
compared to poly (3, 4-ethylenedioxy thiophene) obtained by the
oxidative route.

IT 174508-31-7P, 2 , 5-Dibromo-3, 4-ethylenedioxythiophene

(monomer; prepn. and redox electrochem. of electroactive fully
undoped and sol. oligo (3, 4-ethylenedioxythiophene) s)

RN 174508-31-7 HCA

CN Thieno[3,4-b]-l,4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

IT

RN
CN

163359-60-2P 350037-71-7P

(oligomeric; prepn. and redox electrochem. of electroactive fully
undoped and sol. oligo (3, 4-ethylenedioxythiophene) s)
163359-60-2 HCA

Poly (2, 3-dihydrothieno[3, 4-b] -1 , 4-dioxin-5, 7-diyl) (9CI) (CA INDEX
NAME)

n

Truong 10/728,088

Page 55

RN 350037-71-7 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-ciibromo-2, 3-dihydro-, homopolymer
(9CI) (CA INDEX NAME)

CM 1

CRN 174508-31-7
CMF C6 H4 Br 2 02 S

Br

IT Polymers, preparation

(conjugated; prepn. and redox electrochem. of electroactive fully
undoped and sol. oligo (3, 4-ethylenedioxythiophene) s)

IT Polymerization

(dehalogenation condensation; prepn. and redox electrochem. of
electroactive fully undoped and sol. oligo (3,4-
ethylenedioxythiophene) s)

IT Redox reaction

(electrochem.; prepn. and redox electrochem, of electroactive
fully undoped and sol. oligo (3, 4-ethylenedioxythiophene) s)

IT Polymer chains

(length, conjugation, low homogeneity; prepn. and redox
electrochem. of electroactive fully undoped and sol.
oligo (3, 4-ethylenedioxythiophene) s)

IT Polymers, preparation

(polythiophenes, ethylenedioxythiophene, oligomeric; prepn. and
redox electrochem. of electroactive fully undoped and sol.
oligo (3, 4-ethylenedioxythiophene) s)

IT Conducting polymers

(polythiophenes; prepn. and redox electrochem. of electroactive
fully undoped and sol. oligo (3, 4-ethylenedioxythiophene) s)

IT Conjugation (bond)

Electrochromic materials
Electrochromism
Raman spectra
Redox potential

(prepn. and redox electrochem. of electroactive fully undoped and
sol . oligo (3, 4-ethylenedioxythiophene) s)
IT Band gap

Truong 10/728, 088

Page 56

(semiconductor; prepn. and redox electrochem. of electroactive
fully undoped and sol. oligo (3, 4-ethylenedioxythiophene) s)

IT 182628-58-6, (2,2' -Bipyridine) dibromonickel

(condensation polymn. catalyst; prepn. and redox electrochem. of
electroactive fully undoped and sol. oligo(3,4-
ethylenedioxythiophene) s)

IT 174508-31-7P, 2, 5-Dibromo-3, 4-ethylenedioxythiophene

(monomer; prepn. and redox electrochem. of electroactive fully
undoped and sol. oligo (3, 4-ethylenedioxythiophene) s)

IT 163359-60-2P 350037-71-7P

(oligomeric; prepn. and redox electrochem. of electroactive fully
undoped and sol. oligo (3, 4-ethylenedioxythiophene) s)

IT 128-08-5, N-Bromosuccinimide 126213-50-1, 3,4-
Ethylenedioxythiophene

(prepn. and redox electrochem. of electroactive fully undoped and
sol . oligo (3, 4-ethylenedioxythiophene) s)

IT 127-19-5, N,N-Dimethylacetamide

(solvent; prepn. and redox electrochem. of electroactive fully
undoped and sol. oligo ( 3, 4-ethylenedioxythiophene) s)

L2 6 ANSWER 22 OF 29 HCA COPYRIGHT 2005 ACS on STN

135:68356 Organic electroluminescent device. Nakamura, Kazuaki; Ueda,
Noriko; Yamada, Taketoshi; Kita, Hiroshi (Konica Co., Japan). Jpn.
Kokai Tokkyo Koho JP 2001167885 A2 20010622, 44 pp. (Japanese) .

CODEN : JKXXAF . APPL I CAT? ON
1999-276616 19990929

JP 2000-286785 20000921

GI

CH=CH

AB

PRIORITY: JP

J nl

The invention relates to an org. ellectroluminescent device that
emits in UV-violet region, comprising a polymer represented by I
[R1-R4 = substitution groups; R5 = H or substitution group; k and m
= 0-4 integer; when k and m >2, condensed ring may be formed

Truong 10/728,088

Page 57

among Rl and R2; nl = 1-5/000 integer].
IT 345665-81-8 345666-05-9 345666-11-7

(org. electroluminescent device)
RN 345565-81-8 HCA

CN Magnesium, dibromo [1, 2-ethenediylbis (3-butoxy-5, 2-

thiophenediyl) ] ] di-, polymer with 2, 5-dibromo-3, 4-dibutoxythiophene
(9CI) (CA INDEX NAME)

CM 1

CRN 345665-80-7

CMF C18 H22 Br2 Mg2 02 S2

n-BuO OBu-n

CM 2

CRN 173291-49-1

CMF C12 H18 Br2 02 S

n-BuO OBu-n

RN 345666-05-9 HCA

CN Magnesium, dibromo [jj.- [1, 2-ethenediylbis (3-methyl-5, 2-

thiophenediyl) ] ] di-, polymer with 2, 5-dibromo-3, 4-dimethoxythiophene
(9CI)' (CA INDEX NAME)

CM 1

CRN 345666-04-8
CMF C6 H6 Br2 02 S

Truong 10/728,088 Page 58

MeO

CM 2

CRN 345666-03-7

CMF C12 HIO Br2 Mg2 S2

Me Me

RN 345666-11-7 HCA

CN Magnesium, dibromo [jj.- [1, 2-ethenediylbis (3, 4-dibutoxy-5, 2-

thiophenediyl) ] ] di-, polymer with 2, 5-dibromo-3, 4-dimethoxythiophene
(9CI) (CA INDEX NAME)

CM 1

CRN 345666-10-6

CMF C2 6 H38 Br2 Mg2 04 S2

n-BuO OBu-n

n-BuO OBu-

CM 2

CRN
CMF

345666-04-8
C6 H6 Br2 02 S

Truong 10/728,088 Page 59

MeO OMe

IT Optical filters

(color conversion; org, electroluminescent device)
IT Electroluminescent devices

(org. electroluminescent device)
IT Polyamides, uses

(org. electroluminescent device)
IT 345665-75-0 345665-7 6-1 345665-77-2 345665-79-4
345665-81-8 345665-82-9 34 5565-84-1 34 5665-8 5-2
345 665-8 6-3 34 5665-87-4 34 5665-8 8-5 34 5665-90-9 34 5665-92-1

345665- 94-3 345665-9 6-5 345665-98-7 34 5666-00-4 34 5666-02-6

345666- 05-9 345666-07-1 345666-09-3 345666-11-7
(org. electroluminescent device)

L26 ANSWER 23 OF 29 HCA COPYRIGHT 2005 ACS on STN

133:208463 Molecular Design and Characterization of Chromic Polyfluorene
Derivatives, Blondin, Pierre; Bouchard, Jimmy; Beaupre, Serge;
Belletete, Michel; Durocher, Gilles; Leclerc, Mario (Departement de
Chimie Centre de Recherche en Sciences et Ingenierie des
Macromolecules, Universite Laval, Quebec, QC, GIK 7P4, Can.).
Macromolecules, 33(16), 5874-5879 (English) 2000. CODEN: MAMOBX.
ISSN: 0024-9297. Publisher: American Chemical Society.

AB The thermochromic and solvatochromic properties of a series of

f luorene-based conjugated polymers have been investigated. Both
•poly(2,7-(9, 9-dioctylf luorene) ) and poly (2, 5- (thiophene) -alt-2, 7-
( 9, 9-dioctylf luorene) ) have revealed interesting chromic properties
which, on the basis of theor. calcns., seem to be related to a
relatively flexible backbone. On the other hand, the sterically
hindered, nonplanar poly (2, 5- (3, 4-dimethyl thiophene) -alt-2, 7- (9, 9-
dioctylf luorene) ) does not exhibit any significant solvatochromic
and thermochromic properties which could be explained by an
important energy barrier against planarity. Finally, investigations
on poly (2, 5- (3, 4 -ethylenedioxy thiophene) -alt-2, 7- ( 9, 9-
dioctylf luorene) ) have revealed a highly conjugated conformational
structure which is not significantly modified upon temp, or solvent
changes .

IT 287924-59-8 287924-60-1

(mol. design and characterization of chromic polyfluorene
derivs . )

RN 287924-59-8 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2, 3-dihydro-, polymer with

Truong 10/728,088

Page 60

2, 2 • - (9, 9-dioctyl-9H-fluorene-2, V-diyDbis [4, 4, 5, 5-tetramethyl-l, 3,2-
dioxaborolane] (9CI) (CA INDEX NAME)

CM 1

CRN 196207-58-6
CMF C41 H64 B2 04

Me

CM 2

CRN .174508-31-7
CMF C6 H4 Br2 02 S

RN 287924-60-1 HCA

CN Poly [ (2, 3-dihydrothieno [3, 4-b] -1, 4-dioxin-5, 7-diyl) (9, 9-dioctyl-9H-
fluorene-2, 7-diyl) ] (9CI) (CA INDEX NAME)

Me- (CH2) 7

(CH2) 7-Me

n

Truong 10/728,088

Page 61

IT 174508-31-7P, 2, 5-Dibroino-3, 4-ethylenedioxythiophene

(mol. design and characterization of chromic polyfluorene
derivs . )

RN 174508-31-7 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

IT Polymers, properties

(f luorene-based; mol. design and characterization of chromic
polyfluorene derivs.)
IT Potential barrier
Potential energy
Solvatochromism
Thermochr omi sm
UV and visible spectra

(mol. design and characterization of chromic polyfluorene
derivs . )
IT Bond angle

(torsional; mol. design and characterization of chromic
polyfluorene derivs . )
IT 123864-00-6, Poly (9, 9-dioctylf luorene) 222857-60-5 222857-62-7
287924-57-6 287924-58-7 287924-59-8 287924-60-1

(mol. design and characterization of chromic polyfluorene
derivs . )

IT 3141-26-2, 3, 4-Dibromothiophene

(mol. design and characterization of chromic polyfluorene
derivs . )

IT 74707-05-4P, 2 , 5-Dibromo-3, 4-dimethylthiophene 174508-31-7P
, 2, 5-Dibromo-3, 4-ethylenedioxythiophene

(mol. design and characterization of chromic polyfluorene
derivs . )

L26 ANSWER 24 OF 29 HCA COPYRIGHT 2005 ACS on STN

133:164431 Light-Emitting Diodes from Fluorene-Based 7i-Conjugated

Polymers. Donat-Bouillud, Anne; Levesque, Isabelle; Tao, Ye;

D'lorio, Marie; Beaupre, Serge; Blondin, Pierre; Ranger, Maxime;

Bouchard, Jimmy; Leclerc, Mario (Institute for Microstructural

Sciences, National Research Council of Canada, Ottawa, ON, KIA 0R6,

Truong 10/728, 088

Page 62

Can.). Chemistry of Materials, 12(7), 1931-1936 (English) 2000.
CODEN: CMATEX. ISSN: 0897-4756. Publisher: American Chemical
Society.

The synthesis of f luorene-based 7i-conjugated polymers was carried
out and the electroluminescent properties of the polymers were
studied. The photo- and electroluminescence of poly (dioctylf luorene-
phenylene)s and poly (dioctylf luorene-thiophene) s whose synthesis was
recently published was also studied. The alternate incorporation of
phenylene or thiophene moieties in f luorene-based Tc-conjugated
polymers was used to effect tunability of electroluminescent
properties. The spectral emission varies from blue to green or
yellow, depending on the compn. of the copolymers. To enhance the
luminescence efficiency of polymer assemblies, hole injection and
hole transport into the polymer were improved by insertion* of an
insulating buffer layer and the incorporation of efficient hole
transport material in the polymer. The insertion of a charge
injection layer such as LiF and a hole transport layer such as
N,N' -diphenyl-N, -bis (3-methylphenyl) -1, l-biphenyl-4 , 4 ' -diamine
significantly improved the electroluminescence efficiency of a test
diode from 4.5 to 125 cd/m2 .

174508-31-7P, 2 , 5-Dibromo-3 , 4-ethylenedioxythiophene

(monomer; prepn. of poly (dioctylf luorene-thiophene) s with tunable
electroluminescence and improved carrier transport for use in
light-emitting diodes)

174508-31-7 HCA

Thieno[3,4-b]-l,4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

287924-59-8P 287924-60-lP 287924-61-2P
287924-62-3P

(prepn. of poly (dioctylf luorene-thiophene) s with tunable
electroluminescence and improved carrier transport for use in
light-emitting diodes)
287924-59-8 HCA

Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dibromo-2, 3-dihydro-, polymer with
2,2'- (9, 9-dioctyl-9H-fluorene-2, 7-diyl) bis [4, 4, 5, 5-tetramethyl-l , 3, 2-
dioxaborolane] (9CI) (CA INDEX NAME)

Br

CM

1

Truong 10/728,088

Page 63

CRN 196207-58-6
CMF C41 H64 B2 04

Me-(CH2)7 (CH2)7-Me

0.

CM 2

CRN 174508-31-7
CMF C6 H4 Br2 02 S

Br

Br

RN 287924-60-1 HCA

CN Poly[ (2, 3-dihydrothieno[3,4-b]-l,4-dioxin-5,7-diyl) (9, 9-dioctyl-9H-
fluorene-2, 7-diyl) ] (9CI) (CA INDEX NAME)

Me- (CH2) 7

(CH2)7-Me

n

RN 287924-61-2 HCA

CN 5, 5' -Bithieno [3, 4-b] -1, 4-dioxin, 7,7' -dibromo-2, 2 ' , 3, 3 ' -tetrahydro-,
polymer with 2, 2 ' - (9, 9-dioctyl-9H-f luorene-2, 7-diyl) bis [4 , 4, 5, 5-

Truong 10/728,088

Page 64

tetramethyl-1, 3, 2-dioxaborolane] (9CI)
CM 1

CRN 287924-56-5

CMF C12 H8 Br2 04 S2

(CA INDEX NAME)

CM 2

CRN 196207-58-6
CMF C41 H64 B2 04

Me-(CH2)7 (CH2)7-Me

RN 287924-62-3 HCA

CN Poly [ (2, 2 ' , 3, 3 ' -tetrahydro [5,5' -bithieno [3, 4-b] -1, 4-dioxin] -7,7'
diyl) (9, 9-dioctyl-9H-fluorene-2, 7-diyl) ] (9CI) (CA INDEX NAME)

Truong 10/728; 088

Page 65

Me- (CH2) 7

(CH2)7-Me

n

IT Polymerization

(Suzuki coupling; prepn. of poly (dioctylf luorene-thiophene) s with
tunable electroluminescence and improved carrier transport for
use in light-emitting diodes)

IT Polymers, preparation

(conjugated; prepn. of poly (dioctylf luorene-thiophene) s with
tunable electroluminescence and improved carrier transport for
use in light-emitting diodes)

IT Electroluminescent devices

(light emitting diodes; prepn, of poly (dioctylf luorene-
thiophene)s with tunable electroluminescence and improved carrier
transport for use in light-emitting diodes)

IT Polymers, preparation

(polythiophenes, polyf luorene; prepn. of poly (dioctylf luorene-
thiophene)s with tunable electroluminescence and improved carrier
transport for use in light-emitting diodes)

IT Conducting polymers
Electrochromism
Hole transport

Luminescence, electroluminescence

Oxidation potential

Reduction potential

Suzuki coupling reaction

(prepn. of poly (dioctylf luorene-thiophene) s with tunable
electroluminescence and improved carrier transport for use in
light-emitting diodes)
IT Electric current carriers

(transport; prepn. of poly (dioctylf luorene-thiophene) s with
tunable electroluminescence and improved carrier transport for
use in light-emitting diodes)

Truong 10/728,088 Page 66

7789-24-4, Lithium fluoride (LiF) , properties

(carrier injection layer; prepn. of poly (dioctylf luorene-
thiophene)s with tunable electroluminescence and improved carrier
transport for use in light-emitting diodes)
65181-78-4, N, N' -Diphenyl-N, N' -bis (3-methylphenyl ) -1 , l-biphenyl-4 , 4 ' -
diamine

(hole transport layer; prepn. of poly (dioctylf luorene-thiophene) s
with tunable electroluminescence and improved carrier transport
for use in light-emitting diodes)
195602-1 7- 5P, 2,2' -Bis (3, 4-ethylenedioxy ) bithiophene

(monomer and intermediate; prepn. of poly (dioctylf luorene-
thiophene) s with tunable electroluminescence and improved carrier
transport for use in light-emitting diodes)
74707-05-4P, 2, 5-Dibromo-3, 4-dimethylthiophene 174508-31-7P
, 2, 5-Dibromo-3, 4-ethylenedioxythiophene 287924-56-5P

(monomer; prepn. of poly (dioctylf luorene-thiophene) s with tunable
electroluminescence and improved carrier transport for use in
light-emitting diodes)
7440-05-3, Palladium, uses

(polymn. catalyst; prepn. of poly (dioctylf luorene-thiophene) s
with tunable electroluminescence and improved carrier transport
for use in light-emitting diodes)
1989 64-57-7P 1 98964 -62-4P 2 10347-56- IP 222 8 57- 60- 5P
2228 57-62-7P 222857-64-9P 222857-68-3P 222857- 69-4P
287924-57-6P 287924-58-7P 287924-59-8P
287924-60-lP 287924-61-2P 287924-62-3P

(prepn. of poly (dioctylf luorene-thiophene) s with tunable
electroluminescence and improved carrier transport for use in
light-emitting diodes)
75-16-1, Methylmagnesium bromide 128-08-5, NBS 3141-26-2,
3, 4-Dibromothiophene 126213-50-1, 3, 4-Ethylenedioxythiophene
(prepn. of poly (dioctylf luorene-thiophene) s with tunable
electroluminescence and improved carrier transport for use in
light-emitting diodes)

L26 ANSWER 25 OF 29 HCA COPYRIGHT 2005 ACS on STN

131:74044 Synthesis of non-doped poly (3, 4-ethylenedioxythiophene) and

its spectroscopic data. Yamamoto, Takakazu; Abla, Mahmut (Research
Laboratory of Resources Utilization, Tokyo Institute of Technology,
Yokohama, Japan). Synthetic Metals, 100(2), 237-239 (English) 1999.
CODEN: SYMEDZ. ISSN: 0379-6779. Publisher: Elsevier Science S.A. .

AB Non-doped poly (3, 4-ethylenedioxythiophene) (PEDOTh) has been
synthesized by Ni-promoted dehalogenation polymn. of the
corresponding 2,5-dichloro monomer. Its IR, NMR, and XRD data are
compared with those of PEDOTh prepd. by chem. oxidn. polymn.

IT 225518-49-OP, 2, 5-Dichloro-3, 4-ethylenedioxythiophene

(prepn. and polycondensation of dichloroethylenedioxythiophene
monomer)

f

Truong 10/728,088 Page 67

RN 225518-49-0 HCA

CN Thieno[3, 4-b]-l, 4-dioxin, 5, 7-dichloro-2, 3-dihydro- {9CI) (CA INDEX
NAME)

CI

S

CI

IT 225518-50-3P, 2 , 5-Dichloro-3, 4-ethylenedioxythiophene
homopolymer

(prepn. of undoped polymer by polycondensation)
RN 225518-50-3 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 7-dichloro-2, 3-dihydro-, homopolymer
(9CI) (CA INDEX NAME)

CM 1

CRN 225518-49-0
CMF C6 H4 C12 02 S

CI

IT 163359-60-2P, Poly ( 3, 4-ethylenedioxythiophene-2 , 5-diyl )

(prepn. of undoped polymer by polycondensation of dichloro
monomer)

RN 163359-60-2 HCA

CN Poly(2,3-dihydrothieno[3,4-b]-l,4-dioxin-5,7-diyl) (9CI) (CA INDEX
NAME)

Truong 10/728,088

Page 68

IT Polymerization catalysts

(nickel complex; for polycondensation of

dichloroethylenedioxythiophene monomer)
IT 1295-35-8, Bis (1, 5-cyclooctadiene) nickel

(catalyst for polycondensation of dichloroethylenedioxythiophene)
IT 126213-50-1, 3, 4-Ethylenedioxythiophene

(chlorination; prepn. of dichloroethylenedioxythiophene monomer)
IT 111-78-4, 1,5-Cyclooctadiene 366-18-7, 2, 2 ' -Bipyridyl

(in catalyst for polycondensation of

dichloroethylenedioxythiophene)
IT 225518-49-OP, 2, 5-Dichloro-3, 4-ethylenedioxythiophene

(prepn. and polycondensation of dichloroethylenedioxythiophene

monomer)

IT 225518-50-3P, 2, 5-Dichloro-3, 4-ethylenedioxythiophene
homopolymer

(prepn. of undoped polymer by polycondensation)
IT 163359-60-2P, Poly (3, 4-ethylenedioxythiophene-2 , 5-diyl)

(prepn. of undoped polymer by polycondensation of dichloro
monomer)

L26 ANSWER 26 OF 29 HCA COPYRIGHT 2005 ACS on STN
124:203512 Absorption Properties of Alkoxy-Substituted

Thienylene-Vinylene Oligomers as a Function of the Doping Level.
Havinga, E. E.; Mutsaers, C. M. J.; Jenneskens, L. W. (Philips
Research Laboratories, Eindhoven, 5656 AA, Neth.). Chemistry of
Materials, 8(3), 769-76 (English) 1996. CODEN: CMATEX. ISSN:
0897-4756. Publisher: American Chemical Society.
AB In an attempt to improve on the properties of PEDOT

(poly (3, 4-ethylenedioxythiophene) ) as a stable, conducting, and
transparent coating we synthesized four different alkoxy-substituted
poly ( thienylene-vinylene) s, 1-4, using the Stille coupling reaction.
The oligomers and polymers obtained were characterized and their
NIR-vis absorption spectra were measured as a function of doping,
both electrochem. as films and chem. in soln. Similar spectra of

r

Truong 10/728,088 Page 69

PEDOT films were gathered for comparison. In PEDOT a change in
doping level does not change the energies of the absorption bands,
while for the other polymers the bands shift markedly and the NIR
peak at high doping level lies at a higher energy. The polymers 1-4
are much less suited for the intended coatings than PEDOT. Possible
reasons for this are discussed.

IT 126213-54-5P 173291-56-OP

(absorption properties of alkoxy-substituted thienylene-vinylene
oligomers as a function of the doping level)

RN 126213-54-5 HCA

CN Thieno[3, 4-b] -1, 4-dioxin, 2-hexyl-2, 3-dihydro-, homopolymer (9CI)
(CA INDEX NAME)

CM 1

CRN 126213-53-4
CMF C12 HI 8 02 S

RN 173291-56-0 HCA

CN Stannane, 1, 2-ethenediylbis [ tributyl-, (E)-, polymer with

5, 7-dibromo-2-hexyl-2, 3-dihydrothieno[3, 4-b] -1, 4-dioxin (9CI) (CA
INDEX NAME)

CM 1

CRN 173291-50-4

CMF C12 HI 6 Br2 02 S

CM 2

CRN 14275-61-7

Truong 10/728,088

Page 70

CMF C26 H56 Sn2
Double bond geometry as shown.

(n-Bu) 3Sn'

Sn (Bu-n) 3

IT 126213-51-2, Poly (3, 4-ethylenedioxythiophene)

(absorption properties of alkoxy-substituted thienylene-vinylene

oligomers as a function of the doping level)
RN 126213-51-2 HCA

CN Thieno[3,4-b]-l, 4-dioxin, 2, 3-dihydro-, homopolymer (9CI) (CA INDEX
NAME)

CM 1

CRN 126213-50-1
CMF C6 H6 02 S

IT 173291-48-OP, 2, 5-Dibromo-3, 4-bis (dodecyloxy) thiophene
173291-49-lP, 2, 5-Dibromo-3, 4-dibutoxythiophene
173291-50-4P

(monomer; absorption properties of alkoxy-substituted
thienylene-vinylene oligomers as a function of the doping level)
RN 173291-48-0 HCA

CN Thiophene, 2, 5-dibromo-3, 4-bis (dodecyloxy) - (9CI) (CA INDEX NAME)

Me- (CH2) 11-0

0- (CH2) 11 -Me

RN 173291-49-1 HCA

CN Thiophene, 2, 5-dibromo-3, 4-dibutoxy- (9CI) (CA INDEX NAME)

Truong 10/728,088

Page 71

Br

n-BuO OBu-n

RN 173291-50-4 HCA

CN Thieno [3, 4-b] -1, 4-ciioxin, 5, 7-dibromo-2-hexyl-2, 3-dihydro- (9CI)
(CA INDEX NAME)

IT 173291-52-6P 173291-53-7P 173291-54-8P

173291-55-9P

(oligomeric; absorption properties of alkoxy-substituted
thienylene-vinylene oligomers as a function of the doping level)
RN 173291-52-6 HCA

CN Stannane, 1, 2-ethenediylbis [ tributyl-, (E)-, polymer with

2, 5-dibromo-3, 4-bis (dodecyloxy) thipphene (9CI) (CA INDEX NAME)

CM 1

CRN 173291-48-0

CMF C28 H50 Br2 02 S

Me- (CH2) 11-0

0- (CH2) 11-Me

CM

2

CRN 14275-61-7
CMF C26 H56 Sn2

Double bond geometry as shown.

Truong 10/728,088

Page 72

E

Sn (Bu-n) 3

(n-Bu) 3Sn

RN 173291-53-7 HCA

CN Poly [ [3, 4-bis (dodecyloxy) -2, 5-thiophenediyl] -1, 2-ethenediyl] , (E) -
(9CI) (CA INDEX NAME)

RN 173291-54-8 HCA

CN Stannane, 1, 2-ethenediylbis [tributyl-, (E)-, polymer with
2, 5-dibromo-3, 4-dibutoxythiophene (9CI) (CA INDEX NAME)

CM 1

CRN 173291-49-1

CMF C12 H18 Br2 02 S

Me- (CH2) 11-0

0- (CH2) ll-Me

n

n-BuO

OBu-n

CM

2

CRN
CMF

14275-61-7
C26 H56 Sn2

Double bond geometry as shown.

Sn(Bu-n) 3

RN 173291-55-9 HCA

CN Poly [ (3, 4-dibutoxy-2, 5-thiophenediyl) -1, 2-ethenediyl] , (E)- (9CI)
(CA INDEX NAME)

Truong 10/728, 088

Page 73

S

CH= CH-

n-BuO

OBu-n

n

IT Electric conductivity and conduction
Electric conductors, polymeric
Oscillator strength
Ultraviolet and visible spectra

(absorption properties of alkoxy-substituted thienylene-vinylene
oligomers as a function of the doping level)
IT Infrared spectra

(near-; absorption properties of alkoxy-substituted
thienylene-vinylene oligomers as a function of the doping level)
IT Coating materials

(elec. conductive, transparent, absorption properties of
alkoxy-substituted thienylene-vinylene oligomers as a function of
the doping level)

IT Energy level, band structure

(gap, absorption properties of alkoxy-substituted
thienylene-vinylene oligomers as a function of the doping level)

IT Electric potential

(oxidn., absorption properties of alkoxy-substituted
thienylene-vinylene oligomers as a function of the doping level)

IT Polymers, properties

(polythiophenes, -vinylenes; absorption properties of
alkoxy-substituted thienylene-vinylene oligomers as a function of
the doping level)

IT 126213-54-5P 173291-56-OP 174592-79-lP

(absorption properties of alkoxy-substituted thienylene-vinylene

oligomers as a function of the doping level)
IT 126213-51-2, Poly (3, 4-ethylenedioxythiophene)

(absorption properties of alkoxy-substituted thienylene-vinylene

oligomers as a function of the doping level)
IT 994-89-8P, Tributylethynyltin

(absorption properties of alkoxy-substituted thienylene-vinylene

oligomers as a function of the doping level)
IT 84-58-2, 2, 3-Dicyano-5, 6-dichloro-l , 4-benzoquinone 7705-08-0,
Ferric chloride, reactions

(dopant; absorption properties of alkoxy-substituted

thienylene-vinylene oligomers as a function of the doping level)
IT 128-08-5, N-Bromosuccinimide 120621-18-3, 3- (Dodecyloxy) thiophene

(monomer synthesis; absorption properties of alkoxy-substituted

thienylene-vinylene oligomers as a function of the doping level)

Truong 10/728,088 Page 74

14275-61-7P, (E) -1, 2-Bis ( tributyltin) ethylene 17 3291-47-9P,
2, 5-Dibromo-3- (dodecyloxy) thiophene 173291-48-OP,
2, 5-Dibromo-3, 4-bis (dodecyloxy) thiophene 173291-49-lP,
2, 5-Dibromo-3, 4-dibutoxythiophene 173291-50-4P

(monomer; absorption properties of alkoxy-substituted
thienylene-vinylene oligomers as a function of the doping level)
173291-51-5P, (E) -1, 2-Bis (tributyltin) ethylene-2, S-dibromo-S-
(dodecyloxy) thiophene copolymer 173291-52-6P
173291-53-7P 173291-54-8P 173291-55-9P
174592-80-4P

(oligomeric; absorption properties of alkoxy-substituted
thienylene-vinylene oligomers as a function of the doping level)
14221-01-3, Tetrakis (triphenylphosphine) palladium (0)

(polymn. catalyst; absorption properties of alkoxy-substituted
thienylene-vinylene oligomers as a function of the doping level)
77214-82-5P

(polymn. catalyst; absorption properties of alkoxy-substituted
thienylene-vinylene oligomers as a function of the doping level)

L26 ANSWER 27 OF 29 HCA COPYRIGHT 2005 ACS on STN
124:203135 Electrochromic Conducting Polymers via Electrochemical
Polymerization of Bis (2- (3, 4-ethylenedioxy) thienyl) Monomers.
Sotzing, Gregory A.; Reynolds, John R.; Steel, Peter J. (Center for
Macromolecular Science and Engineering, University of Florida,
Gainesville, FL, 32611, USA). Chemistry of Materials, 8(4), 882-9
(English) 1996. CODEN: CMATEX. ISSN: 0897-4756. Publisher:
American Chemical Society.
AB A series of bis (2- (3, 4-ethylenedioxy) thiophene) -based monomers were
synthesized and fully characterized; specifically
(E) -1, 2-bis (2- (3, 4-ethylenedioxy) thienyl ) vinylene (BEDOT-V) ,

1. 4- bis (2- (3, 4-ethylenedioxy) thienyl ) benzene (BEDOT-B) ,

4, 4 ' -bis (2- (3, 4-ethylenedioxy) thienyl ) biphenyl (BEDOT-BP) ,

2. 5- bis (2- (3, 4-ethylenedioxy) thienyl) furan, 2, 5-bis (2- (3, 4-
ethylenedioxy) thienyl) -thiophene (BEDOT-T) , and 2, 2 ' : 5 ^ 2 ^ * -ter (3, 4-
ethylenedioxy) thiophene, TER-EDOT. The X-ray crystal structures of
BEDOT-V and BEDOT-B were detd. These monomers oxidize and
polymerize at low potentials relative to other reported
electropolymerizable heterocycles . The electroactive polymers
formed have low redox switching potentials and are quite stable in
the conducting state. TER-EDOT had the lowest peak oxidn. potential
of +0.2 V vs Ag/Ag+, making it the most easily oxidized
polymerizable thiophene monomer reported. The electronic band gaps
of these EDOT based polymers were 1.4-2.3 eV (measured as the onset
of the TT-Ti* transition) offering a diverse range of colors

which may prove useful in electrochromic devices. For example,
poly (BEDOT-V) is deep purple and opaque in the reduced state and
transmissive sky blue in the oxidized state, poly (BEDOT-T) is deep
blue opaque in the reduced state and transmissive blue in the

Truong 10/728,088 Page 75

oxidized state, while poly (BEDOT-BP) is transmissive orange in the
reduced state and opaque purple in the oxidized state. A thin film
of poly (BEDOT-V) switched rapidly between redox states (under 2 s)
with an initial optical contrast of 43%. This polymer retained 47%
of its optical contrast and 48% of its original charge d. after 600
double potential steps.

IT 162899-00-5P 168641-47-2P 168641-48-3P
174508-35-lP 174508-36-2P 174508-37-3P

(electrochromic conducting polymers via electrochem. polymn. of
bis (ethylenedioxy) thienyl) monomers)

RN 162899-00-5 HCA

CN Thieno[3, 4-b]-l, 4-dioxin, 5, 5'- (1, 2-ethenediyl) bis [2, 3-dihydro-,
(E)-, homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 162898-99-9
CMF C14 H12 04 S2

Double bond geometry as shown.

RN 168641-47-2 HCA

CN Thieno[3, 4-b] -1, 4-dioxin, 5, 5'- (1, 4-phenylene) bis [2, 3-dihydro-,
homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 168641-43-8
CMF C18 H14 04 S2

Truong 10/728,088

Page 7 6

RN 168641-48-3 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5, 5 ' - ( [1, 1 ' -biphenyl] -4, 4 ' -diyl) bis [2,3-
dihydro-, homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 168641-44-9
CMF C24 H18 04 S2

RN 174508-35-1 HCA

CN 5,5' :7',5' ' -Terthieno [3, 4-b] -1, 4-dioxin, 2, 2', 2' ',3, 3', 3' ' -hexahydro-
, homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 174508-34-0
CMF C18 H14 06 S3

RN 174508-36-2 HCA

CN Thieno [3, 4-b] -1, 4-dioxin, 5,5'- (2, 5-furandiyl) bis [2, 3-dihydro-,
homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 174508-32-8
CMF C16 H12 05 S2

Truong 10/728,088

Page 77.

RN 174508-37-3 HCA

CN Thieno[3, 4-b] -1, 4-dioxin, 5, 5' - (2, 5-thiophenediyl) bis [2, 3-dihydro-,
homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 174508-33-9
CMF C16 H12 04 S3

0.

IT

RN
CN

174508-31-7P

(intermediate; electrochromic conducting polymers via
electrochem. polymn. of bis (ethylenedioxy) thienyl) monomers)
174508-31-7 HCA

Thieno[3,4-b]-l,4-dioxin, 5, 7-dibromo-2, 3-dihydro- (9CI) (CA INDEX
NAME)

Br

IT Bond angle
Bond length
Crystal structure
Electric conductors, polymeric

(electrochromic conducting polymers via electrochem. polymn. of
bis (ethylenedioxy) thienyl) monomers)
IT Polymerization

(electrochem., electrochromic conducting polymers via
electrochem. polymn. of bis (ethylenedioxy) thienyl ) monomers)
IT Energy level, band structure

Truong 10/728,088 Page 78

(gap, electrochromic conducting polymers via electrochem. polymn.
of bis (ethylenedioxy) thienyl) monomers)
Polymers, preparation

(polythiophenes, electrochromic conducting polymers via
electrochem. polymn. of bis (ethylenedioxy) thienyl) monomers)
Crystallography

(x-ray, electrochromic conducting polymers via electrochem.
polymn. of bis (ethylenedioxy) thienyl) monomers)
162899-00-5P 168641-47-2P 168641-48-3P
174508-35-lP 174508-36-2P 174508-37-3P

(electrochromic conducting polymers via electrochem. polymn. of
bis (ethylenedioxy) thienyl) monomers)
32460-00-7P, 2, 5-Dibromof uran . 162898-99-9P 168641-43-8P
174508-31-7P

(intermediate; electrochromic conducting polymers via
electrochem. polymn. of bis (ethylenedioxy ) thienyl ) monomers)
168 641-4 4-9P 174 508-32-8P 174508- 33-9P 174 508-34-OP

(monomer; electrochromic conducting polymers via electrochem.
polymn. of bis (ethylenedioxy) thienyl) monomers)
106-37-6, p-Dibromobenzene. 110-00-9, Furan 156-60-5
3141-27-3, 2, 5-Dibromothiophene 126213-50-1, 3,4-
Ethylenedioxythiophene

(starting material; electrochromic conducting polymers via
electrochem. polymn. of bis (ethylenedioxy) thienyl) monomers)

L26 ANSWER 28 OF 29 HCA COPYRIGHT 2005 ACS on STN

123:286791 The synthesis of decyloxy substituted poly ( 1 , 2-ethynediyl-2 , 5-
thiophenediyls) . McKellar, B. R.; Feld, William A. (Department
Chemistry, Wright State University, Dayton, OH, 45435, USA) .
Polymer Preprints (American Chemical Society, Division of Polymer
Chemistry), 35(2), 680-1 (English) 1994. CODEN: ACPPAY. ISSN:
0032-3934. Publisher: American Chemical Society, Division of
Polymer Chemistry.

AB An improved prepn. of 2 , 5-diethynyl-3, 4-didecyloxythiophene (I) is

reported. 1 was polymd. with 2, 5-dibromo-3, 4-didecyloxythiophene or
2, 5-dibromothiophene to give polymers with thermal stability
<200° .

IT 169826-78-2P

(prepn. and polymn. of decyloxy-substituted thiophenes)

RN 169826-78-2 HCA

CN Thiophene, 3, 4-bis (decyloxy) -2, 5-diethynyl-, polymer with

2, 5-dibromo-3, 4-bis (decyloxy) thiophene (9CI) (CA INDEX NAME)

CM 1

CRN 169826-77-1

CMF C24 H42 Br2 02 S

Truong 10/728,088 Page 79

Me- (CH2) 9-0 0- (CH2) 9-Me

CM

CRN 152189-52-1
CMF C28 H44 02 S

Me-(CH2)9-0 0-(CH2)9-Me

IT 152189-52-lP

(prepn. and polymn. of decyloxy-substituted thiophene)
IT 169826-78-2P 169826-79-3P

(prepn. and polymn. of decyloxy-substituted thiophenes)

L2 6 ANSWER 29 OF 29 HCA COPYRIGHT 2005 ACS on STN

122:315261 Synthesis and characterization of thiophenes, oligothiophenes
and polythiophenes with crown ether units in direct
7t-conjugation. Baeuerle, P.; Scheib, St. (Inst. Organische
Chemie, Universitaet Wuerzburg, Wuerzburg, D-97074, Germany) . Acta
Polymerica, 46(2), 124-9 (English) 1995. CODEN: ACPODY. ISSN:
0323-7648. Publisher: VCH.

GI

Truong 10/728,088 Page 80

AB I (R,R' = 2-thiophenyl; R,R' = H; R = H, R' = 2-thiophenyl ) were
prepd. by substitution of I (R,R' = Br) with 2-
(trimethylstannyl) thiophene/ deacylation of I (R,R' =
ethyloxycarbonyl) , and substitution of I (R = H, R' =
trimethylstannyl) . I (R,R' = H; R = H, R' = 2-thiophenyl) were
polymd. potentiodynamically to prep, selectively conducting
polythiophenes with crown ether units in direct 7t-conjugation,
The redox behavior of polymer films was characterized by cyclic
voltammograms in MeCN solns. in the presence of Li+, Na+, and K+
cations, and by spectroelectrochem. measurements. The redox
behavior of I (R,R' = H) polymer was effected by the introduction of
cations, whereas that of I (R = H, R' = 2-thiophenyl) polymer was
not. The sensitivity of I (R,R' = H) polymer to cations increased
in the order: Na+ » Li+ > K+.

IT 163657-78-lP 163657-79-2P

(prepn. and electrochem. properties of thiophenes and
polythiophenes with crown ether units in direct ^-conjugation)

RN 163657-78-1 HCA

CN Thieno [3, 4-b] -1,4,7, 10, 13-pentaoxacyclopentadecin,

2, 3, 5, 6, 8, 9, 11, 12-octahydro-, homopolymer (9CI) (CA INDEX NAME)

CM 1

CRN 122372-74-1
CMF C12 HI 8 05 S

RN 163657-79-2 HCA

CN Thieno [3, 4-b] -1, 4,7,10, 13-pentaoxacyclopentadecin,

2,3,5,6,8,9,ll,12-octahydro-14-(2-thienyl)-, homopolymer (9CI) (CA
INDEX NAME) •

CM 1

CRN
CMF

163657-76-9
C16 H20 05 S2

Truong 10/728, 088

Page 81

IT 163657-74-7P

(prepn. and electrochem. properties of thiophenes and
polythiophenes with crown ether units in direct 7i-conjugation)
RN 163657-74-7 HCA

CN Thieno [3, 4-b] -1,4,7, 10, 13-pentaoxacyclopentadecin,

14, 16-dibromo-2, 3, 5, 6, 8, 9, 11, 12-octahydro- (9CI) (CA INDEX NAME)

Br

IT Electric conductors, polymeric
Electric current

(prepn, and electrochem. properties of thiophenes and
polythiophenes with crown ether units in direct 7i-conjugation)

IT Polymerization

(electrochem., prepn. and electrochem. properties of thiophenes
and polythiophenes with crown ether units in direct
7c-conjugation)

IT Electric potential

(oxidn., prepn. and electrochem. properties of thiophenes and
polythiophenes with crown ether units in direct K-conjugation)

IT Polymers, preparation

(polythiophenes, crown ether group-contg . , prepn. and
electrochem. properties of thiophenes and polythiophenes with
crown ether units in direct 7r-conjugation)

IT 3109-63-5, Tetrabutylammonium hexaf luorophosphate 7601-89-0,

Sodium perchlorate 7791-03-9, Lithium perchlorate 17084-13-8,
Potassium hexaf luorophosphate

(prepn. and electrochem. properties of thiophenes and
polythiophenes with crown ether units in direct Tc-conjugation)

IT 163 657-7 6-9P 163657-77-OP

(prepn. and electrochem. properties of thiophenes and
polythiophenes with crown ether units in direct 7c-conjugation}

IT 163657~78-1P 163657-79-2P

Truong 10/728,088 Page 82

(prepn. and electrochem. properties of thiophenes and
polythiophenes with crown ether units in direct 7r-conjugation)

IT 1066-45-1, Trimethylstannyl chloride 3437-95-4, 2-Iodothiophene
37496-13-2, 2- (Trimethylstannyl) thiophene 122372-64-9
(prepn. and electrochem. properties of thiophenes and
polythiophenes with crown ether units in direct 7i-conjugation)

IT 163657-75-8P

(prepn. and electrochem. properties of -thiophenes and
polythiophenes with crown ether units in direct Ti-conjugation)

IT 163657-74-7P

(prepn. and electrochem. properties of thiophenes and
polythiophenes with crown ether units in direct Tt-conjugation)

=>